Benzohetero cyclylcyclo hexenones and their use as herbicides

ABSTRACT

The invention relates to cyclohexenone derivatives of benzo-condensed, unsaturated 5-ring nitrogen heterocycles of general formula (I) wherein X represents N or a group C—R 3 , Y represents O, S, SO, SO 2  or NR 4  or X—Y represent S═N and X represents sulfur, and the variables R 1 , R 2  and Hex have the meanings given in claim  1 . The invention also relates to a method for producing these compounds, to agents containing these compounds, and to their use as herbicides.

This application is a 371 of PCT/EP00/04042 May 5, 2000.

The present invention relates to cyclohexenone derivatives ofbenzo-fused unsaturated 5-membered nitrogen heterocycles, to processesfor preparing such cylohexenone derivatives, to compositions comprisingsuch compounds, and to the use of the cyclohexenone derivatives or ofthe compositions comprising them for controlling harmful plants.

WO 96/05182 discloses saccharin derivatives having herbicidal actionwhich are substituted on the benzene ring of the saccharin skeleton by a(2-cyclohexane-1,3-dione)carbonyl radical.

WO 99/03845 discloses cyclohexane-1,3-diones which have a benzoylradical in the 2-position. The benzoyl radical for its part can besubstituted by heteroaromatic compounds. The compounds have herbicidalaction.

WO 97/09324 discloses cyclohexane-1,3-diones having herbicidal actionwhich have a benzo-fused sulfur heterocycle, for example a thiochromaneor a benzodihydrothiophene radical, which is attached via a carbonylgroup, in the 2-position.

EP-A 283 261 discloses similar compounds in which the cyclohexenone ringis substituted in the 2-position by a heteroaromatic radical. Theheteroaromatic radicals mentioned are sulfur-, nitrogen- and/oroxygen-containing 5-membered or 6-membered heterocycles.

However, the herbicidal properties of the compounds known from thepublications mentioned and their compatibility with crop plants do notmeet all of the criteria required from herbicides.

It is an object of the present invention to provide novel compoundshaving herbicidal action which preferably have greater activity than theherbicidal substances of the prior art and/or better selectivity withrespect to harmful plants.

We have found that this object is achieved by cyclohexenone derivativesof benzo-fused unsaturated 5-membered nitrogen heterocycles of theformula I defined below.

Consequently, the present invention relates to cyclohexenone derivativesof benzo-fused unsaturated 5-membered nitrogen heterocyles of theformula I,

in which

X is N or a group C—R³;

Y is O, S, SO, SO₂ or NR⁴

or

X-Y is S═N, and X is sulfur;

R¹ is hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl,C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, ordi-(C₁-C₆-alkyl)amino-C₁-C₆-alkyl;

R² is hydrogen, halogen or C₁-C₆-alkyl;

R³ is hydrogen, halogen, nitro, cyano, hydroxyl, amino, mercapto,thiocyanato, hydrazide, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-hydroxyalkyl, C₁-C₆-aminoalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-hydroxyalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,

is C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino, wherethe alkyl and cycloalkyl groups of the three last-mentioned radicals maybe partially or fully halogenated and/or may carry one to threesubstituents selected from the group consisting of C₁-C₄-alkoxy orhydroxyl,

is C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-hydroxyalkylthio,C₁-C₆-alkoxy-C₁-C₆-alkylthio,

is phenyl, naphthyl, heterocyclyl, phenoxy, phenylamino, diphenylamino,where the phenyl and heterocyclyl groups of the six last-mentionedradicals for their part may be partially or fully halogenated and/or maycarry one, two or three substituents selected from the group consistingof nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy,

is C(O)OR⁵, or C(O)N(R⁶)R⁷; and

R⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl,

is phenyl, naphthyl, where the two last-mentioned radicals for theirpart may be partially or fully halogenated and/or may carry one, two orthree substituents selected from the group consisting of nitro, cyano,hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; where

R⁵ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl,

is phenyl, naphthyl or heterocyclyl, where the three last-mentionedradicals for their part may be partially or fully halogenated and/or maycarry one, two or three substituents selected from the group consistingof nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy;

R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,

are phenyl or naphthyl, where the two last-mentioned radicals for theirpart may be partially or fully halogenated and/or may carry one, two orthree substituents selected from the group consisting of nitro, cyano,hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; and

Hex is substituted (3-oxo-1-cyclohexen-2-yl)carbonyl of the formula IIaor is substituted (1,3-dioxo-2-cyclohexyl)methylidene of the formula IIb

 where the variables R⁸ to R¹⁴ are as defined below:

R⁸ is hydroxyl, mercapto, halogen, OR¹⁵, SR¹⁵, SOR¹⁶, SO₂R¹⁶, OSO₂R¹⁶,P(O)R¹⁷R¹⁸, OP(O)R¹⁷R¹⁸, P(S)R¹⁷R¹⁸, OP(S)R¹⁷R¹⁸, NR¹⁹R²⁰, ONR¹⁹R²⁰ orN-bonded heterocyclyl which may be partially or fully halogenated and/ormay carry one to three of the following radicals: nitro, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R⁹, R¹³ independently of one another are hydrogen, C₁-C₄-alkyl orC₁-C₄-alkoxycarbonyl;

R¹⁰, R¹², R¹⁴ independently of one another are hydrogen or C₁-C₄-alkyl;

R¹¹ is hydrogen, halogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,di(C₁-C₆-alkoxy)methyl, (C₁-C₆-alkoxy)(C₁-C₆-alkylthio)methyl,di(C₁-C₆-alkylthio)methyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl;

is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl,1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the sixlast-mentioned radicals may be substituted by one to three C₁-C₄-alkylradicals;

or

R¹⁰ and R¹² or R¹² and R¹⁴ together form a n bond or a C₁-C₅-alkyl chainwhich may carry one, two or three radicals from the following group:halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl;

or

R¹⁰ and R¹⁴ together form a C₁-C₄-alkyl chain which may carry one, twoor three radicals from the following group: halogen, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl;

or

R¹¹ and R¹² together form a —O—(CH₂)_(p)—O—, —O—(CH₂)_(p)—S—,—S—(CH₂)_(p)—S—, —O—(CH2)_(q)— or —S—(CH2)_(q)— chain in which p is 2,3, 4 or 5 and q is 2, 3, 4, 5 or 6, which may be substituted by one, twoor three radicals from the following group: halogen, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C4-alkoxycarbonyl;

or

R¹¹ and R¹² together with the carbon to which they are attached form acarbonyl group;

where

R¹⁵ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl,C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl,C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl,C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl,C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl,C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₁-C₆-alkoxy)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkoxy)aminocarbonyl,N-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkoxy)aminocarbonyl,di(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, wherethe alkyl, cycloalkyl or alkoxy radicals mentioned may be partially orfully halogenated and/or may carry one, two or three of the followinggroups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino.,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl,C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl,phenylaminocarbonyl, N-(C₁-C₆-alkyl)-N-phenylaminocarbonyl,phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl,heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,heterocyclylaminocarbonyl, N-(C₁-C₆-alkyl)-N-heterocyclylaminocarbonylor heterocyclyl-C₁-C₆-alkenylcarbonyl, where the phenyl or theheterocyclyl radical of the 18 last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or C₃-C₆-cycloalkyl,where the four radicals mentioned may be partially or fully halogenatedand/or may carry one, two or three of the following groups: cyano,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl,

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl,where the phenyl or the heterocyclyl radical of the four last-mentionedsubstituents may be partially or fully halogenated and/or may carry one,two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹⁷, R¹⁸ independently of one another are hydrogen, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkylor phenoxy, where the three last-mentioned substituents may be partiallyor fully halogenated and/or may carry one, two or three of the followingradicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl,hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, amino,C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino,where the alkyl, cycloalkyl or alkoxy radicals mentioned may bepartially or fully halogenated and/or may carry one, two or three of thefollowing radicals: cyano, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl orC₃-C₆-cycloalkyl,

is phenyl, phenyl-C₁-C₄ -alkyl, phenylcarbonyl, heterocyclyl,heterocyclyl-C₁-C₄-alkyl or heterocyclylcarbonyl, where the phenyl orheterocyclyl radical of the six last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R²⁰ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

and their agriculturally useful salts.

Furthermore, we have found herbicidal compositions which comprise thecyclohexenone derivatives of the formula I and have very good herbicidalaction. Moreover, we have found processes for preparing thesecompositions and methods for controlling undesirable vegetation usingthe cyclohexenone derivatives of the formula I.

Depending on the substitution pattern, the compounds of the formula Imay contain one or more chiral centers, in which case they are presentenantiomers or diastereomer mixtures. The invention provides both thepure enantiomers or diastereomers and their mixtures.

The compounds of the formula I may also be present in the form of theiragriculturally useful salts, the type of salt generally beingimmaterial. In general, the salts of those cations or the acid additionsalts of those acids are suitable whose cations and anions,respectively, do not negatively affect the herbicidal action of thecompounds I.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium and potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium, where,if desired, 1 to 4 hydrogen atoms may be replaced by C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfoniumand sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

For R⁸=hydroxyl or mercapto {Z=O,S}, IIa also represents the tautomericforms IIa′, IIa″ and IIa′″,

and IIb also represents the tautomeric forms IIb′, IIb″ and IIb′″.

The organic molecular moieties mentioned for the substituents R¹ to R²⁰or as radicals on phenyl and heterocyclyl radicals are collective termsfor individual enumerations of the particular group members. Allhydrocarbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy,alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, N-alkylamino, N,N-dialkylamino,N-haloalkylamino, N-alkoxyamino, N-alkoxy-N-alkylamino,N-alkylcarbonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy,alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl,alkoxyalkyl, alkoxyiminoalkyl, phenylalkylcarbonyl,heterocyclylalkylcarbonyl, phenylalkenylcarbonyl,heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl,N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl,phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl,heterocyclylcarbonylalkyl, alkoxyalkoxycarbonyl, alkenylcarbonyl,alkenyloxycarbonyl, alkenylaminocarbonyl,N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl,alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl,N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl,alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy,alkanediyl, alkenediyl, alkadienediyl or alkynediyl moieties can bestraight-chain or branched. Unless indicated otherwise, halogenatedsubstituents preferably carry one to five identical or different halogenatoms. The expression halogen represents in each case fluorine,chlorine, bromine or iodine.

Examples of other meanings are:

C₁-C₄-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl,1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;

C₁-C₆-alkyl, and the alkyl moieties of C₁-C₆-alkylamino,di(C₁-C₆-alkyl)amino, N-(C₁-C₆-alkoxy)-N-(C₁-C₆-alkyl)amino,N-(C₁-C₆-alkoxy)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkyl)aminocarbonyl,(C₃-C₆-alkynyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₁-C₆-alkyl)-N-phenylaminocarbonyl,N-(C₁-C₆-alkyl)-N-heterocyclylaminocarbonyl: C₁-C₄-alkyl as mentionedabove, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, chloromethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl,2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl,2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutylor nonafluorobutyl;

C₁-C₆-haloalkyl, and the haloalkyl moieties of N-C₁-C₆-haloalkylamino:C₁-C₄-haloalkyl, as mentioned above, and also, for example,5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,6-iodohexyl or dodecafluorohexyl;

C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy,butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;

C₁-C₆-alkoxy, and the alkoxy moieties of N-C₁-C₆-alkoxyamino,N-(C₁-C₆-alkoxy)-N-(C₁-C₆-alkyl)amino, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,N-(C₁-C₆-alkoxy)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkoxy)aminocarbonyl andN-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkoxy)aminocarbonyl: C₁-C₄-alkoxy asmentioned above, and also, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, fluoromethoxy, difluoromethoxy,trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy,2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy or nonafluorobutoxy;

C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy as mentioned above, and also, forexample, 5-fluoropentoxy, 5-chloropelntoxy, 5-bromopentoxy,5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy,6-bromohexoxy, 6iodohexoxy or dodecafluorohexoxy;

C₁-C₄-alkylthio (C₁-C₄-alkylsulfanyl: C₁-C₄-alkyl-S—): for examplemethylthio, ethylthio, propylthio, 1-methylethylthio, butylthio,1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;

C₁-C₆-alkylthio, and the alkylthio moieties of C₁-C₆-alkylthiocarbonyl:C₁-C₄-alkylthio as mentioned above, and also, for example, pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or1-ethyl-2-methylpropylthio;

C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned above whichis partially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, fluoromethylthio, difluoromethylthio,trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio,2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio,3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio,4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio ornonafluorobutylthio;

C₁-C₆-haloalkylthio: C₁-C₄-haloalkylthio as mentioned above, and also5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio ordodecafluorohexylthio;

C₁-C₄-alkylsulfinyl (C₁-C₄-alkyl-S(═O)—): for example, methylsulfinyl,ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl,1-methylpropylsulfinyl, 2-methylpropylsulfinyl or1,1-dimethylethylsulfinyl;

C₁-C₆-alkylsulfinyl: C₁-C₄-alkylsulfinyl as mentioned above, and alsopentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl,3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl,1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl,2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl,1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;

C₁-C₄-haloalkylsulfinyl: a C₁-C₄-alkylsulfinyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, i.e., for example, fluoromethylsulfinyl,difluoromethylsulfinyl, trifluoromethylsulfinyl,chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl,2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl,2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl,3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl,2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl,heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl,1-(chloromethyl)-2-chloroethylsulfinyl,1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl;

C₁-C₆-haloalkylsulfinyl: C₁-C₄-haloalkylsulfinyl as mentioned above, andalso 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl,5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl,6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl,6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;

C₁-C₄-alkylsulfonyl (C₁-C₄-alkyl-S(═O)₂—): for example methylsulfonyl,ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl,1-methylpropylsulfonyl, 2-methylpropylsulfonyl or1,1-dimethylethylsulfonyl;

C₁-C₆-alkylsulfonyl: C₁-C₄-alkylsulfonyl, as mentioned above, and alsopentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,1-iethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,2-methylpentylsulfonyl , 3-methylpentylsulfonyl, 4-methylpentylsulfonyl,1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl,1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl,2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl,1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;

C₁-C₄-haloalkylsulfonyl: a C₁-C₄-alkylsulfonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, i.e., for example, fluoromethylsulfonyl,difluoromethylsulfonyl, trifluoromethylsulfonyl,chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl,2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,2,2,2-trifluoroethylsulfonyl, 2-chloto-2-fluoroethylsulfonyl,2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl,3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl,heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl,1-(chloromethyl)-2-chloroethylsulfonyl,1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl;

C₁-C₆-haloalkylsulfonyl: C₁-C₄-haloalkylsulfonyl as mentioned above, andalso 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl,5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl,6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;

C₁-C₆-alkylamino: methylamino, ethylamino, propylamino,1-methylethylamino, butylamino, 1-methylpropylamino,2-methylpropylamino, 1,1-dimethylethylamino, pentylamino,1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino,2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino,1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino,2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino,2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino,1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino,1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or1-ethyl-2-methylpropylamino;

di(C₁-C₄-alkyl)amino: for example N,N-dimethylamino, N,N-diethylamino,N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino,N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino,N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino,N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino,N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino,N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino,N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino,N-(1-methylethyl)-N-(1-methylpropyl)amino,N-(1-methylethyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino,N-butyl-N-(1,1-dimethylethyl)amino,N-(1-methylpropyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino orN-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;

di(C₁-C₆-alkyl)amino: di(C₁-C₄-alkyl)amino as mentioned above, and alsoN,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino,N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino;

C₁-C₄-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl,propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl,1-methylpropylcarbonyl, 2-methylpropylcarbonyl or1,1-dimethylethylcarbonyl;

C₁-C₆-alkylcarbonyl, and the alkylcarbonyl radicals ofC₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino:C₁-C₄-alkylcarbonyl as mentioned above, and also, for example,pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl,3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl,1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl,1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl,2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl,1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl,1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl,2,3-dimethylbutylcarbonyl, 3,3-dimethyibutylcarbonyl,1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;

C₁-C₄-haloalkylcarbonyl: a C₁-C₄-alkylcarbonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, i.e. for example, chloroacetyl, dichloroacetyl,trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl,chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl,2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl,2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl,2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl,2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl,2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl,2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl,2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl,2-chloropropylcarbonyl, 3-chloropropylcarbonyl,2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl,3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl,3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl,heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl,1-(chloromethyl)-2-chloroethylcarbonyl,1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl,4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl;

C₁-C₆-haloalkylcarbonyl: a C₁-C₄-haloalkylcarbonyl radical as mentionedabove, and also 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl,5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorohexylcarbonyl,6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or perfluorohexylcarbonyl;

C₁-C₄-alkoxycarbonyl: i.e, for example, methoxycarbonyl, ethoxycarbonyl,propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl,1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or1,1-dimethylethoxycarbonyl;

C₁-C₆-alkoxycarbonyl: C₁-C₄-alkoxycarbonyl as mentioned above, and also,for example, pentoxycarbonyl, 1-methylbutokycarbonyl,2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl,1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,2,,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl;

C₁-C₄-haloalkoxycarbonyl: a C₁-C₄-alkoxycarbonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, i.e., for example, fluoromethoxycarbonyl,difluoromethoxycarbonyl, trifluoromethoxycarbonyl,chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl,2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl,2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl,2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl,2-chlorb-2,2-difluoroethoxycarbonyl,2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl,pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl,3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl,3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl,2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl,3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl,heptafluoropropoxycarbonyl, 1-(fluoromethyl)-2-fluoroethoxycarbonyl,1-(chloromethyl)-2-chloroethoxycarbonyl,1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl,4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl or 4-iodobutoxycarbonyl;

C₁-C₆-halooxycarbonyl: a C₁-C₄-halooxycarbonyl radical as mentionedabove, and also 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl,5-bromopentoxydarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonylor 6-bromohexoxycarbonyl;

(C₁-C₄-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy,propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy,1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or1,1-dimethylethylcarbonyloxy;

(C₁-C₄-alkylamino)carbonyl: for example methylaminocarbonyl,ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl,butylaminocarbonyl, 1-methylpropylaminocarbonyl,2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;

(C₁-C₆-alkylamino)carbonyl: (C₁-C₄-alkylamino)carbonyl as mentionedabove, and also, for example, pentylaminocarbonyl,1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl,1-ethylpropylaminocarbonyl, hexylaminocarbonyl,1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl,1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl,3-methylpentylaminocarbonyl, 4-methylpentylaminodarbonyl,1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl,1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl,2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl,1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl,1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl,1-ethyl-1-methylpropylaminocarbonyl or1-ethyl-2-methylpropylaminocarbonyl;

di(C₁-C₄-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl,N,N-diethylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl,N,N-dipropylaminocarbonyl, N,N-dibutylaminocarbonyl,N,N-di(1-methylpropyl)aminocarbonyl,N,N-di(2-methylpropyljaminocarbonyl,N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl,N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl,N-methyl-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-methylaminocarbonyl,N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl,N-ethyl-N-(2-methylpropyl)aminocarbonyl,N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl,N-(1-methylpropyl)-N-propylaminocarbonyl,N-(2-methylpropyl)-N-propylaminocarbonyl,N-(1,1-dimethylethyl)-N-propylaminocarbonyl,N-butyl-N-(1-methylethyl)aminocarbonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,N-butyl-N-(1-methylpropyl)aminocarbonyl,N-butyl-N-(2-methylpropyl)aminocarbonyl,N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl orN-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;

di(C₁-C₆-alkyl)aminocarbonyl: di(C₁-C₄-alkyl)aminocarbonyl as mentionedabove, and also, for example, N-methyl-N-pentylaminocarbonyl,N-methyl-N-(1-methylbutyl)aminocarbonyl,N-methyl-N-(2-methylbutyl)aminocarbonyl,N-methyl-N-(3-methylbutyl)aminocarbonyl,N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl,N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-hexylaminocarbonyl,N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl,N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl,N-methyl-N-(1-methylpentyl)aminocarbonyl,N-methyl-N-(2-methylpentyl)aminocarbonyl,N-methyl-N-(3-methylpentyl)aminocarbonyl,N-methyl-N-(4-methylpentyl)aminocarbonyl,N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl,N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl,N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl,N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl,N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl,N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl,N-methyl-N-(1-ethylbutyl)aminocarbonyl,N-methyl-N-(2-ethylbutyl)aminocarbonyl,N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,N-ethyl-N-pentylaminocarbonyl, N-ethyl-N-(1-methylbutyl)aminocarbonyl,N-ethyl-N-(2-methylbutyl)aminocarbonyl,N-ethyl-N-(3-methylbutyl)aminocarbonyl,N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl,N-ethyl-N-(1-ethylpropyl)aminocarbonyl, N-ethyl-N-hexylaminocarbonyl,N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl,N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl,N-ethyl-N-(1-methylpentyl)aminocarbonyl,N-ethyl-N-(2-methylpentyl)aminocarbonyl,N-ethyl-N-(3-methylpentyl)aminocarbonyl,N-ethyl-N-(4-methylpentyl)aminocarbonyl,N-ethyl-N-(1,l-dimethylbutyl)aminocarbonyl,N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl,N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl,N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl,N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl,N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl,N-ethyl-N-(1-ethylbutyl)aminocarbonyl,N-ethyl-N-(2-ethylbutyl)aminocarbonyl,N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl,N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl,N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl orN,N-dihexylaminocarbonyl;

di(C₁-C₆-alkyl)aminothiocarbonyl: for exampleN,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl,N,N-di(1-methylethyl)aminothiocarbonyl, N,N-dipropylaminothiocarbonyl,N,N-dibutylaminothiocarbonyl, N,N-di(1-methylpropyl)aminothiocarbonyl,N,N-di(2-methylpropyl)aminothiocarbonyl,N,N-di(1,1-dimethylethyl)aminothiocarbonyl,N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl,N-methyl-N-(1-methylethyl)aminothiocarbonyl,N-butyl-N-methylaminothiocarbonyl,N-methyl-N-(1-methylpropyl)aminothiocarbonyl,N-methyl-N-(2-methylpropyl)aminothiocarbonyl,N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl,N-ethyl-N-propylaminothiocarbonyl,N-ethyl-N-(1-methylethyl)aminothiocarbonyl,N-butyl-N-ethylaminothiocarbonyl,N-ethyl-N-(1-methylpropyl)aminothiocarbonyl,N-ethyl-N-(2-methylpropyl)aminothiocarbonyl,N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl,N-(1-methylethyl)-N-propylaminothiocarbonyl,N-butyl-N-propylaminothiocarbonyl,N-(1-methylpropyl)-N-propylaminothiocarbonyl,N-(2-methylpropyl)-N-propylaminothiocarbonyl,N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl,N-butyl-N-(1-methylethyl)aminothiocarbonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl,N-butyl-N-(1-methylpropyl)aminothiocarbonyl,N-butyl-N-(2-methylpropyl)aminothiocarbonyl,N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl,N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl,N-methyl-N-pentylaminothiocarbonyl,N-methyl-N-(1-methylbutyl)aminothiocarbonyl,N-methyl-N-(2-methylbutyl)aminothiocarbonyl,N-methyl-N-(3-methylbutyl)aminothiocarbonyl,N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,N-methyl-N-(1-ethylpropyl)aminothiocarbonyl,N-methyl-N-hexylaminothiocarbonyl,N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,N-methyl-N-(-methylpentyl)aminothiocarbonyl,N-methyl-N-(2-methylpentyl)aminothiocarbonyl,N-methyl-N-(3-methylpentyl)aminothiocarbonyl,N-methyl-N-(4-methylpentyl)aminothiocarbonyl,N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(1-ethylbutyl)aminothiocarbonyl,N-methyl-N-(2-ethylbutyl)aminothiocarbonyl,N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,N-methyl-N-(1,2,2-trimethyl propyl)aminothiocarbonyl,N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,N-ethyl-N-pentylaminothiocarbonyl,N-ethyl-N-(1-methylbutyl)aminothiocarbonyl,N-ethyl-N-(2-methylbutyl)aminothiocarbonyl,N-ethyl-N-(3-methylbutyl)aminothiocarbonyl,N-Ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl,N-ethyl-N-hexylaminothiocarbonyl,N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1-methylpentyl)aminothiocarbonyl,N-ethyl-N-(2-methylpentyl)aminothiocarbonyl,N-ethyl-N-(3-methylpentyl)aminothiocarbonyl,N-ethyl-N-(4-methylpentyl)aminothiocarbonyl,N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl,N-ethyl-N-(12-ethylbutyl)aminothiocarbonyl,N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl,N,N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl,N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl orN,N-dihexylaminothiocarbonyl;

C₁-C₆-hydroxyalkyl: C₁-C₆-alkyl which is substituted by one to three OHgroups, for example hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl,1,2-bishydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl,4-hydroxybutyl, 2,2-dimethyl-3-hydroxypropyl;

phenyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by a phenylradical, for example benzyl, 1-phenylethyl and 2-phenylethyl, where thephenyl radical may, in the manner mentioned, be partially or fullyhalogenated or may carry one to three of the substituents mentionedabove for phenyl; correspondingly, heterocyclyl-C₁-C₆-alkyl is aC₁-C₆-alkyl which is substituted by a heterocyclyl radical;

C₁-C₆-alkoxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted byC₁-C₆-alkoxy as mentioned above, i.e., for example, methoxymethyl,ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl,(1-methylpropoxy)methyl, (2-methylpropoxy)methyl,(1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl,2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl,2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl,2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl,3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl,3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or4-(1,1-dimethylethoxy)butyl;

C₁-C₆-alkoxy-C₁-C₆-alkoxy, and the alkoxyalkoxy moieties ofC₁-C₆-alkoxy-C₁-C₆-alkoxycarbonyl: C₁-C₆-alkoxy which is substituted byC₁-C₆-alkoxy as mentioned above, i.e, for example, methoxymethoxy,ethoxymethoxy, propoxymethoxy, (1-methylethoxy)methoxy, butoxymethoxy,(1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy,(1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy,2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy,2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy,2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy,2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy,2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy,3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy,3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy,2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy,2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy,2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy,3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy,3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy,4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy,4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or4-(1,1-dimethylethoxy)butoxy;

C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by aC₁-C₆-alkylcarbonyl group, where both of the C₁-C₆-alkyl groups maycarry one or more substituents selected from C₁-C₄-alkoxy and/orhydroxyl: for example acetylmethyl (=2-oxopropyl), 2-(acetyl)ethyl(=3-oxo-n-butyl), 3-oxo-n-pentyl, 1,1-dimethyl-2-oxopropyl,3-hydroxy-2-oxopropyl or 3-hydroxy-2-oxobutyl;

C₃-C₆-alkenyl, and the alkenyl moieties of C₃-C₆-alkenylcarbonyl,C₃-C₆-alkenyloxy, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkenylaminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkoxy)aminocarbonyl: for exampleprop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl,2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl, 1-penten-4-yl,2-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl,3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,3-methyl-but-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, hex-3-en-1-yl,hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-3-en-1-yl,2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl,4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl,1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl,1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl,1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl,2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or1-ethyl-2-methylprop-2-en-1-yl;

C₂-C₆-alkenyl, and the alkenyl moieties of C₂-C₆-alkenylcarbonyl,phenyl-C₂-C₆-alkenylcarbonyl and heterocyclyl-C₂-C₆-alkenylcarbonyl:C₃-C₆-alkenyl as mentioned above, and also ethenyl;

C₃-C₆-haloalkenyl: a C₃-C₆-alkenyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, 2-chloroallyl, 3-chloroallyl,2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl,2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl,3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;

C₃-C₆-alkynyl, and the alkynyl moieties of C₃-C₆-alkynylcarbonyl,C₃-C₆-alkynyloxy, C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkynylaminocarbonyl,N-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkoxy)aminocarbonyl: for example propargyl,but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3 -yl,pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl,pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl,hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl,hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl,hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl,3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-ylor methylpent-2-yn-5-yl;

C₂-C₆-alkynyl, and the alkynyl moieties of C₂-C₆-alkynylcarbonyl:C₃-C₆-alkynyl as mentioned above, and also ethynyl;

C₃-C₆-haloalkynyl: a C₃-C₆-alkynyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl,3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl,1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;

C₁-C₆-alkanediyl: methanediyl, ethane-1,1-diyl, ethane-1,2-diyl,propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2-diyl,butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl,2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl,2-methylpropane-1,1-diyl, 1-methylpropane-1,2-diyl,1-methylpropane-2,2-diyl, 1-methylpropane-1,1-diyl, pentane-1,1-diyl,pentane-1,2-diyl, pentane-1,3-diyl, pentane-1,5-diyl, pentane-2,3-diyl,pentane-2,2-diyl, 1-methylbutane-1,1-diyl, 1-methylbutane-1,2-diyl,1-methylbutane-1,3-diyl, 1-methylbutane-1,4-diyl,2-methylbutane-1,1-diyl, 2-methylbutane-1,2-diyl,2-methylbutane-1,3-diyl, 2-methylbutane-1,4-diyl,2,2-dimethylpropane-1,1-diyl, 2,2-dimethylpropane-1,3-diyl,1,1-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,2-diyl,2,3-dimethylpropane-1,3-diyl, 2,3-dimethylpropane-1,2-diyl,1,3-dimethylpropane-1,3-diyl, hexane-1,1-diyl, hexane-1,2-diyl,hexane-1,3-diyl, hexane-1,4-diyl, hexane-1,5-diyl, hexane-1,6-diyl,hexane-2,5-diyl, 2-methylpentane-1,1-diyl, 1-methylpentane-1,2-diyl,1-methylpentane-1,3-diyl, 1-methylpentane-1,4-diyl,1-methylpentane-1,5-diyl, 2-methylpentane-1,1-diyl,2-methylpentane-1,2-diyl, 2-methylpentane-1,3-diyl,2-methylpentane-1,4-diyl, 2-methylpentane-1,5-diyl,3-methylpentane-1,1-diyl, 3-methylpentane-1,2-diyl,3-methylpentane-1,3-diyl, 3-methylpentane-1,4-diyl,3-methylpentane-1,5-diyl, 1,1-dimethylbutane-1,2-diyl,1,1-dimethylbutane-1,3-diyl, 1,1-dimethylbutane-1,4-diyl,1,2-dimethylbutane-1,1-diyl, 1,2-dimethylbutane-1,2-diyl,1,2-dimethylbutane-1,3-diyl, 1,2-dimethylbutane-1,4-diyl,1,3-dimethylbutane-1,1-diyl, 1,3-dimethylbutane-1,2-diyl,1,3-dimethylbutane-1,3-diyl, 1,3-dimethylbutane-1,4-diyl,1-ethylbutane-1,1-diyl, 1-ethylbutane-1,2-diyl, 1-ethylbutane-1,3-diyl,1-ethylbutane-1,4-diyl, 2-ethylbutane-1,1-diyl, 2-ethylbutane-1,2-diyl,2-ethylbutane-1,3-diyl, 2-ethylbutane-1,4-diyl, 2-ethylbutane-2,3-diyl,2,2-dimethylbutane-1,1-diyl, 2,2-dimethylbutane-1,3-diyl,2,2-dimethylbutane-1,4-diyl, 1-isopropylpropane-1,1-diyl,1-isopropylpropane-1,2-diyl, 1-isopropylpropane-1,3-diyl,2-isopropylpropane-1,1-diyl, 2-isopropylpropane-1,2-diyl,2-isopropylpropane-1,3-diyl, 1,2,3-trimethylpropane-1,1-diyl,1,2,3-trimethylpropane-1,2-diyl or 1,2,3-trimethylpropane-1,3-diyl;

C₂-C₆-alkenediyl: ethene-1,1-diyl, ethene-1,2-diyl, 1-propene-1,1-diyl,1-propene-1,2-diyl, 1-propene-1,3-diyl, 2-propene-1,1-diyl,2-propene-1,2-diyl, 2-propene-1,3-diyl, 1-butene-1,1-diyl,1-butene-1,2-diyl, 1-butene-1,3-diyl, 1-butene-1,4-diyl,2-butene-1,1-diyl, 2-butene-1,2-diyl, 2-butene-1,3-diyl,2-butene-1,4-diyl, 3-butene-1,1-diyl, 3-butene-1,2-diyl,3-butene-1,3-diyl, 3-butene-1,4-diyl, 1-methyl-1-propene-1,2-diyl,1-methyl-1-propene-1,3-diyl, 1-methyl-2-propene-1,1-diyl,1-methyl-2-propene-1,2-diyl, 1-methyl-2-propene-1,3-diyl,2-methyl-1,1-propene-1,1-diyl, 2-methyl-1-propene-1,3-diyl,3-butene-1,1-diyl, 3-butene-1,2-diyl, 3-butene-1,3-diyl,3-butene-1,4-diyl, 1-pentene-1,1-diyl, 1-pentene-1,2-diyl,1-pentene-1,3-diyl, 1-pentene-1,4-diyl, 1-pentene-1,5-diyl,1-hexene-1,1-diyl, 1-hexene-1,2-diyl, 1-hexene-1,3-diyl,1-hexene-1,4-diyl, 1-hexene-1,5-diyl or 1-hexene-1,6-diyl;

C₂-C₆-alkadienediyl: 1,3-butadiene-1,1-diyl, 1,3-butadiene-1,2-diyl,1,3-butadiene-1,3-diyl, 1,3-butadiene-1,4-diyl, 1,3-pentadiene-1,1-diyl,1,3-pentadiene-1,2-diyl, 1,3-pentadiene-1,3-diyl,1,3-pentadiene-1,4-diyl, 1,3-pentadiene-1,5-diyl,2,4-pentadiene-1,1-diyl, 2,4-pentadiene-1,2-diyl,2,4-pentadiene-1,3-diyl, 2,4-pentadiene-1,4-diyl,2,4-pentadiene-1,5-diyl, 1-methyl-1,3-butadiene-1,4-diyl,1,3-hexadiene-1,1-diyl, 1,3-hexadiene-1,2-diyl, 1,3-hexadiene-1,3-diyl,1,3-hexadiene-1,4-diyl, 1,3-hexadiene-1,5-diyl, 1,3-hexadiene-1,6-diyl,1-methyl-1,3-pentadiene-1,2-diyl, 1-methyl-1,3-pentadiene-1,3-diyl,1-methyl-1,3-pentadiene-1,4-diyl or 1-methyl-1,3-pentadiene-1,5-diyl;

C₂-C₆-alkynediyl: ethyne-1,2-diyl, 1-propyne-1,3-diyl,2-propyne-1,1-diyl, 2-propyne-1,3-diyl, 1-butyne-1,3-diyl,1-butyne-1,4-diyl, 2-butyne-1,1-diyl, 2-butyne-1,4-diyl,1-methyl-2-propyne-1,1-diyl, 1-methyl-2-propyne-1,3-diyl,1-pentyne-1,3-diyl, 1-pentyne-1,4-diyl, 1-pentyne-1,5-diyl,2-pentyne-1,1-diyl, 2-pentyne-1,4-diyl, 2-pentyne-1,5-diyl,3-pentyne-1,1-diyl, 3-pentyne-1,2-diyl, 3-pentyne-1,5-diyl,4-pentyne-1,1-diyl, 4-pentyne-1,2-diyl, 4-pentyne-1,3-diyl,4-pentyne-1,5-diyl, 1-hexyne-1,3-diyl, 1-hexyne-1,4-diyl,1-hexyne-1,5-diyl, 1-hexyne-1,6-diyl, 2-hexyne-1,1-diyl,2-hexyne-1,4-diyl, 2-hexyne-1,5-diyl, 2-hexyne-1,6-diyl,3-hexyne-1,1-diyl, 3-hexyne-1,2-diyl, 3-hexyne-1,5-diyl,3-hexyne-1,6-diyl, 4-hexyne-1,1-diyl, 4-hexyne-1,2-diyl,4-hexyne-1,3-diyl, 4-hexyne-1,6-diyl, 5-hexyne-1,1-diyl,5-hexyne-1,2-diyl, 5-hexyne-1,3-diyl, 5-hexyne-1,4-diyl or5-hexyne-1,6-diyl;

C₃-C₆-cyclbalkyl, and the cycloalkyl moieties of C₃-C₆-cycloalkylaminoand C₃-C₆-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl; heterocyclyl, and the heterocyclyl moietiesof heterocyclyloxy, heterocyclylcarbonyl, heterocyclyl-C₁-C₄-alkyl,heterocyclyl-C₁-C₆-alkyl, heterocyclylsulfonyl orheterocyclyloxysulfonyl, heterocyclyloxycarbonyl,heterocyclyloxythiocarbonyl, heterocyclyl-C₂-C₆-alkenylcarbonyl,heterocyclylcarbonyl-C₁-C₆-alkyl,N-(C₁-C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,heterocyclylaminocarbonyl: a saturated, partially saturated orunsaturated 5- or 6-membered heterocyclic ring which contains one, two,three or four identical or different heteroatoms selected from thefollowing group: oxygen, sulfur or nitrogen, i.e., for example, C-bonded5-membered rings such as:

tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl,tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl,2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl,2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl,2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl,2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl,2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl,4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl,3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl,3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl,3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl,tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl,tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl,1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl,tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl,1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl,tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl,tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl,tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl,1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl,1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl,4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl,2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl,2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl,4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl,2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl,2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl,2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl,4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl,4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl,2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl,2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl,2,3-dihydroisothiazol-5-yl, Δ³-1,2-dithiol-3-yl, Δ³-1,2-dithiol-4-yl,Δ³-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl,4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl,2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl,2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl,2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl,4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl,2,5-dihydrookazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl,4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl,2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl,2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl,2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl,1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl,1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl,isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl,oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl,thiazol-5-yl, 1,2,3-Δ²-oxadiazolin-4-yl, 1,2,3-Δ²-oxadiazolin-5-yl,1,2,4-Δ⁴-oxadiazolin-3-yl, 1,2,4-Δ⁴-oxadiazolin-5-yl,1,2,4-Δ²-oxadiazolin-3-yl, 1,2,4-Δ²-oxadiazolin-5-yl,1,2,4-Δ³-oxadiazolin-3-yl, 1,2,4-Δ³-oxadiazolin-5-yl,1,3,4-Δ²-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-5-yl,1,3,4-Δ³-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl,1,2,4-Δ⁴-thiadiazolin-3-yl, 1,2,4-Δ⁴-thiadiazolin-5-yl,1,2,4-Δ³-thiadiazolin-3-yl, 1,2,4-Δ³-thiadiazolin-5-yl,1,2,4-Δ²-thiadiazolin-3-yl, 1,2,4-Δ²-thiadiazolin-5-yl,1,3,4-Δ²-thiadiazolin-2-yl, 1,3,4-Δ²-thiadiazolin-5-yl,1,3,4-Δ³-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl,1,3,2-dioxathiolan-4-yl, 1,2,3-Δ²-triazolin-4-yl,1,2,3-Δ²-triazolin-5-yl, 1,2,4-Δ²-triazolin-3-yl,1,2,4-Δ²-triazolin-5-yl, 1,2,4-Δ³-triazolin-3-yl,1,2,4-Δ³-triazolin-5-yl, 1,2,4-Δ¹-triazolin-3-yl, 1,2,4-triazolin-3-yl,3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl,2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl,1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-triazol-4-yl,1,2,4-triazol-3-yl, tetrazol-5-yl;

C-bonded 6-membered rings such as:

tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl,piperidin-2-yl, piperidin-3-yl, piperidin-4-yl,tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl,2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl,2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl,2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl,2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl,2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl,1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl,1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl,2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl,2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl,2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl,2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl,2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl,1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl,1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl,1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl,2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl,2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl,4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl,4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl,1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl,2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl,2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl,2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl,1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl,1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl,3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl,3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl,3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl,2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl,2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl,2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl,2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl,2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,I,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl,1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl,1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl,1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yI,1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-ylhexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl,hexahydropyridazin-3-yl, hexahydropyridazin-4-yl,tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl,tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl,tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl,tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl,tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-ylitetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl,tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl,tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl,2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl,2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl,2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl,2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl,4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl,4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl,4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl,4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl,2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl,2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl,2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl,2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl,2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl,2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl,2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl,2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl,2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl,2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl,3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl,1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl,1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl,1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl,4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl,4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl,4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl,4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl,3,4,5,6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl,3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl,1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl,1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl,1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl,2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl,2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl,2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl,2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl,2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl,4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl,4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl,4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl,6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl,6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl,2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl,2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl,2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl,4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl,4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl,4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl,6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl,6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl,2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl,2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl,2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl,4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl,1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl,1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl,1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl,1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl,1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl,1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl,1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl,3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl,3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl,pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl,1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,1,2,4-triazin-6-yl or 1,2,4,5-tetrazin-3-yl;

N-bonded 5-membered rings such as:

tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl,2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl,tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl,tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl,4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl,2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl,2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl,2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl,2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl,2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl,imidazol-1-yl, 1,2,4-Δ⁴-oxadiazolin-2-yl, 1,2,4-Δ²-oxadiazolin-4-yl,1,2,4-Δ³-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-4-yl,1,2,4-Δ⁵-thiadiazolin-2-yl, 1,2,4-Δ³-thiadiazolin-2-yl,1,2,4-Δ²-thiadiazolin-4-yl, 1,3,4-Δ²-thiadiazolin-4-yl,1,2,3-Δ²-triazolin-1-yl, 1,2,4-Δ²-triazolin-1-yl,1,2,4-Δ²-triazolin-4-yl, 1,2,4-Δ³-triazolin-1-yl,1,2,4-Δ¹-triazolin-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl,tetrazol-1-yl;

N-bonded 6-membered rings such as:

piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl,1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl,1,2-dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl,hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl,tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl,tetrahydro-1,4-oxazin-4-yl (morpholinyl), tetrahydro-1,2-oxazin-2-yl,2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl,2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-2-yl,2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl,1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl,1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl,1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl,1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl,2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl,4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl,1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or3,4-dihydropyrimidin-3-yl;

and also N-bonded cyclic imides such as:

phthalimide, tetrahydrophthalimide, succinimide, maleimide, glutarimide,5-oxotriazolin-1-yl, 5-oxo-1,3,4-oxadiazolin-4-yl or2,4-dioxo(1H,3H)pyrimidin-3-yl;

 where, if appropriate, the sulfur of the heterocycles mentioned may beoxidized to S═O or S(═O)₂

and where a bicyclic ring system may be formed with a fused-on phenylring or with a C₃-C₆-carbocycle or with a further 5- to 6-memberedheterocycle.

All phenyl rings or heterocyclyl radicals and all phenyl components inphenoxy, phenylalkyl, phenylcarbonylalkyl, phenylcarbonyl,phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,phenylaminocarbonyl and N-alkyl-N-phenylaminocarbonyl, phenylsulfonyl orphenoxysulfonyl or heterocyclyl components in heterocyclyloxy,heterocyclylalkyl, heterocyclylcarbonylalkyl, heterocyclylcarbonyl,heterocyclyloxythiocarbonyl, heterocyclylalkenylcarbonyl,heterocyclyloxycarbonyl, heterocyclylaminocarbonyl,N-alkyl-N-heterocyclylaminocarbonyl, heterocyclylsulfonyl orheterocyclyloxysulfonyl are, unless stated otherwise, preferablyunsubstituted, or they carry one, two or three halogen atoms and/or anitro group, a cyano radical and/or one or two methyl, trifluoromethyl,methoxy or trifluoromethoxy substituents.

With regard to the use of the compounds of the formula I according tothe invention as herbicides, the variables X, Y, R¹ to R²⁰ preferablyhave the following meanings, in each case on their own or incombination:

R¹ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkyloxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxyalkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, particularlypreferably methyl, chlorine, methoxy, methylthio, methylsulfinyl,methylsulfonyl, bromomethyl, methoxymethyl, methylsulfonylmethyl;

R² is hydrogen, halogen, for examplechlorine or bromine, C₁-C₆-alkyl,for example methyl;

X is C—R³ where R³ is as defined above, or is N;

Y is S, SO₂ or N—R⁴ where R⁴ is as defined above;

Hex is a radical of the formula IIa, where R⁸, R⁹, R¹⁰, R¹¹ R¹², R¹³ andR¹⁴ are as defined above.

Preference is given, in particular, to compounds of the formula I whereY is O, S, SO₂ or N—R⁴ and X is C—R³. Preference is also given tocompounds of the formula I where X is N and Y is S or N—R⁴.

R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³ and R¹⁴ are preferably as defined below:

R⁸ is hydroxyl, halogen, mercapto, OR¹⁵, SR¹⁵, SO₂R¹⁶, OSO₂R¹⁶, NR¹⁹R²⁰,ONR¹⁹R²⁰ or N-bonded heterocyclyl which may be partially or fullyhalogenated and/or may carry one, two or three of the followingradicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; in particular hydroxyl, OR¹⁵, SR¹⁵, N(OR¹⁹)R²⁰;particularly preferably hydroxyl, C₁-C₄-alkyloxy, di-C₁-C₄-alkylamino,N-C₁-C₄-alkoxy-C₁-C₄-alkylamino, C₁-C₄-alkylthio, phenylthio,O—CH₂-phenyl, phenylcarbonyloxy, 2-, 3- or 4-fluorophenylcarbonyloxy,C₁-C₄-sulfonyloxy, phenylsulfonyloxy and 2-, 3- or4-methylphenylsulfonyloxy;

R⁹, R¹³ are hydrogen or C₁-C₄-alkyl, such as methyl, ethyl or propyl;preferably hydrogen or methyl;

R¹⁰, R¹², R¹⁴ are hydrogen or C₁-C₄-alkyl, such as methyl, ethyl orpropyl; preferably hydrogen or methyl;

R¹¹ is hydrogen, hydroxyl, C₁-C₆-alkyl, di(C₁-C₆-alkoxy)methyl,(C₁-C₆-alkoxy)(C₁-C₆-alkylthio)methyl, di(C₁-C₆-alkylthio)methyl,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl;

is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl,1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the sixlast-mentioned radicals may be substituted by one, two or threeC₁-C₄-alkyl radicals;

preferably hydrogen, hydroxyl or C₁-C₄-alkyl, such as methyl, ethyl orpropyl;

or

R¹⁰ and R¹² or R¹² and R¹⁴ together form a n bond or a C₃-C₅-alkyl chainwhich may carry one to three radicals selected from the following group:halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl orC₁-C₄-alkoxycarbonyl;

or

R¹⁰ and R¹⁴ or R⁹ and R¹³ together form a C₁-C₄-alkyl chain which maycarry one to three radicals selected from the following group: halogen,cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl orC₁-C₄-alkoxycarbonyl;

or R¹¹ and R¹² together form a —O—(CH₂)_(p)—O—, —O—(CH₂)_(p)—S— orS—(CH₂)_(p)—S— chain which may be substituted by one to three radicalsselected from the following group: halogen, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; particularly preferably, R²⁰and R²¹ together form a —O—(CH₂)_(p)—O—, —O—(CH₂)_(p)—S— or—S—(CH₂)_(p)—S— chain which may be substituted by one to three radicalsselected from the following groups: C₁-C₄-haloalkyl orC₁-C₄-alkoxycarbonyl;

or

R¹¹ and R¹² together with the carbon to which they are attached form acarbonyl group. The variable p preferably represents 2 or 3 and thevariable q preferably represents 2, 3 or 4.

Preferred meanings for R¹⁵ to R²⁰ are:

R¹⁵ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl,C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₃-C₆-cycloalkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl,C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl,C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl,C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₁-C₆-alkoxy)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkoxy)aminocarbonyl,N-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkoxy)aminocarbonyl,di(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, wherethe alkyl, cycloalkyl or alkoxy radicals mentioned may be partially orfully halogenated and/or may carry one to three of the following groups:cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl,C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl,phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl,heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl orheterocyclyl-C₁-C₆-alkenylcarbonyl, where the phenyl or the heterocyclylradical of the 14 last-mentioned substituents may be partially or fullyhalogenated and/or may carry one to three of the following radicals:nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

is preferably C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl orN,N-di(C₁-C₆-alkyl)aminocarbonyl, where the alkyl or alkoxy radicalsmentioned may be partially or fully halogenated and/or may carry one tothree of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio orC₁-C₄-alkoxycarbonyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,phenylcarbonyl, phenoxycarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl orheterocyclyloxycarbonyl, where the phenyl or the heterocyclyl radical ofthe 10 last-mentioned substituents may be partially or fully halogenatedand/or may carry one to three of the following radicals: nitro, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-cycloalkyl, where the threeradicals mentioned may be partially or fully halogenated and/or maycarry one to three of the following groups: cyano, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl;

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl,where the phenyl or the heterocyclyl radical of the four last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following radicals: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹⁷, R¹⁸ are hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, phenyl,phenyl-C₁-C₄-alkyl or phenoxy, where the three last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following radicals: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹⁹ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyloxy or di(C₁-C₆-alkyl)amino, where the alkyl,cycloalkyl or alkoxy radicals mentioned may be partially or fullyhalogenated and/or may carry one to three of the following radicals:cyano, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl,di(C₁-C4-alkyl)aminocarbonyl or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl, heterocyclyl,heterocyclyl-C₁-C₄-alkyl or heterocyclylcarbonyl, where the phenylor-heterocyclyl radical of the six last-mentioned substituents may be,partially or fully halogenated and/or may carry one to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R²⁰ is C₁-C₆-alkyl or C₃-C₆-alkenyl.

Particular preference is given to compounds of the formula I where X isC—R³ and

R³ is hydrogen, halogen, cyano, thiocyanato, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkyl,

is phenyl or pyridyl, where the two last-mentioned radicals may bepartially or fully halogenated and/or may carry one, two or three, inparticular one, of the following radicals: halogen, C₁-C₄-alkoxy,C₁-C₄-haloalkyl, and C₁-C₄-haloalkoxy;

or

is COOR⁵ where R⁵ is as defined above. Here, R⁵ is in particularhydrogen or C₁-C₆-alkyl and particularly preferably hydrogen, methyl,ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert-butyl.

Preference is also given to the compounds of formula I where X is C—R³where R³ is cyclopropyl or phenoxy which may be substituted as statedfor phenyl.

Examples of preferred radicals R³ are hydrogen, fluorine, chlorine,bromine, cyano, thiocyanato, methyl, ethyl, n-propyl, isopropyl,n-butyl, 2-butyl, isobutyl, tert-butyl, chloromethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,2,2,2-trifluoroethyl, methoxymethyl, ethoxymethyl, methoxy, ethoxy,1-propoxy, 2-propoxy, 1-butoxy, 2-butoxy, 2-methylprop-1-oxy,tert-butyloxy, difluoromethyloxy, trifluoromethyloxy,2,2,2-trifluoroethyl-1-oxy, (methoxy)methyloxy, methylsulfanyl,ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, 1-butylsulfanyl,2-butylsulfanyl, 2-methylprop-1-ylsulfanyl, tert-butylsulfanyl,fluoromethylsulfanyl, trifluoromethylsulfanyl,2,2,2-trifluoroethyl-1-sulfanyl, 2-(methylcarbonyl)ethyl, phenyl,phenoxy, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2-, 3-or-4-hydroxyphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or4-(trifluoromethoxy)phenyl, 2-, 3- or 4-(difluoromethoxy)phenyl, 2-, 3-or 4-(trifluoromethyl)phenyl, 2-, 3- or 4-tolyl, 2-, 3- or4-fluorophenoxy, 2-, 3- or 4-methoxyphenoxy, 2-, 3- or4-trifluoromethylphenoxy, 2-, 3- or 4-chlorophenoxy, 2-, 3- or4-pyridinyl, methoxycarbonyl, ethoxycarbonyl, trifluoromethoxycarbonyl,isopropoxycarbonyl, tert-butoxycarbonyl and phenoxycarbonyl.

Very particularly preferred compounds of the formula I where X=C—R³ arethose compounds where R³ is hydrogen, halogen, in particular fluorine orchlorine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, in particular fluoromethyl,difluoromethyl, trifluoromethyl and 2,2,2-trifluoroethyl, or phenylwhere the phenyl radical may carry one, two or three, in particular one,substituent(s), selected from the group consisting of C₁-C₄-alkyl, inparticular methyl, halogen, in particular fluorine or chlorine,C₁-C₄-alkoxy, in particular methoxy, or haloalkoxy, in particulartrifluoromethoxy.

Among the cyclohexenone derivatives of the formula I mentioned above,particular preference is given to those compounds which are derived frombenzothiazole-5-carboxylic acid, i.e. compounds of the formula I where Xis a radical C—R³ and Y is selected from the group consisting of S, SOand SO₂. In turn, among the cyclohexenone derivatives of benzothiazolepreference is given to those where R³ has one of the meanings mentionedabove as being preferred. In particular, Y is S or SO₂.

Preference according to the invention is also given.to thosecyclohexenone derivatives which are derived frombenzoxazole-5-carboxylic acid, i.e. compounds of the formula I where Xis a group C—R³ where R³ is as defined above and Y is an oxygen atom.Among these, in turn, preference is given to those compounds where R³has the meanings given above as being preferred.

Preference is also given to cyclohexenone derivatives of the formula Iwhich are derived from benzimidazole-5-carboxylic acid, i.e. compoundsof the formula I where X is C—R³ where R³ is as defined above and Y is agroup N—R⁴ where R⁴ is as defined above. Among these, preference isgiven to those benzimidazole derivatives of the formula I where R³ hasthe meanings given above as being preferred for R³. Furthermore,preference is given to benzimidazole derivatives of the formula I whereR⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl, in particular hydrogen,methyl, ethyl, n-propyl or isopropyl.

Preference according to the invention is also given to cyclohexenonederivatives of benzotriazole-5-carboxylic acid, i.e. compounds of theformula I where X is nitrogen and Y is a group N—R⁴ where R⁴ is asdefined above. Among these, in turn, preference is given to thosecompounds where R⁴ has the meanings given above as being preferred.

Preference according to the invention is also given to cyclohexenonederivatives of benzothiadiazole-5-carboxylic acid, i.e. compounds of theformula I where X is N and Y is S. Preference is also given to pyrazolederivatives of benzoisothiadiazolecarboxylic acid, i.e. compounds of theformula I where X-Y is S═N and X is S.

Particular preference is given to the compounds of the formula I where

R⁸ is hydroxyl.

Likewise, particular preference is given to the compounds of the formulaI where

R⁸ is halogen, OR¹⁵, SR¹⁵, SO₂R¹⁶, OSO₂R¹⁶, NR¹⁹R²⁰, N(OR¹⁹)R²⁰ orN-bonded heterocyclyl which may be partially or fully halogenated and/ormay carry one to three of the following radicals: nitro, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

Very particular preference is given to the compounds of the formula Iwhere the variables in formula IIa or IIb are as defined below:

R⁹, R¹³ are hydrogen or C₁-C₄-alkyl;

R¹⁰, R¹², R¹⁴ are hydrogen or C₁-C₄-alkyl;

R¹¹ is hydrogen, hydroxyl, C₁-C₆-alkyl, in particular C₁-C₄-alkyl,di(C₁-C₆-alkoxy)methyl, (C₁-C₆-alkoxy)(C₁-C₆-alkylthio)methyl,di(C₁-C₆-alkylthio)methyl, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl; in particular hydrogen,hydroxyl or C₁-C₆-alkyl;

or

R⁹ and R¹³ or R¹⁰ and R¹⁴ together form a C₁-C₄-alkyl chain which maycarry one to three radicals selected from the following group: halogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl; in particular, R¹⁰ and R¹⁴ together forma methylene or ethylene bridge which may carry one or two radicalsselected from the following group: halogen, C₁-C₂-alkyl orC₁-C₂-haloalkyl;

or

R¹¹ and R¹² together with the carbon to which they are attached form acarbonyl group.

Most preference is given to the compounds of the formula I where R⁹,R¹⁰, R¹¹, R¹², R¹³ and R¹⁴ independently of one another are hydrogen orC₁-C₄-alkyl,

R¹¹ can also be hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, haloalkoxy orhaloalkylthio,

R¹¹ and R¹² together with the carbon atom to which they are attached mayalso be a carbonyl group, a 1,3-dioxolane, 1,3-dithiolane,1,3-oxothiolane, 1,3-oxothiane, 1,3-dithiolane or a 1,3-dithiane ring,where the 2-position of the six rings mentioned is identical to thecarbon atom to which R¹¹ and R¹² are attached,

R⁹ and R¹³ or R¹⁰ and R¹⁴ may also be a C₁-C₄-alkylene chain,

R¹⁰ and R¹² or R¹² and R¹³ together may form a π a bond.

Most preference is also given to the compounds of the formula I where

R⁹, R¹³ are hydrogen or C₁-C₄-alkyl;

R¹⁰, R¹², R¹⁴ are hydrogen or C₁-C₄-alkyl;

R¹¹ is hydrogen, hydroxyl, C₁-C₆-alkyl, di(C₁-C₆-alkoxy)methyl,(C₁-C₆-alkoxy)(C₁-C₆-alkylthio)methyl, di(C₁-C₆-alkylthio)methyl,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl orC₁-C₆-haloalkylsulfonyl; in particular hydrogen, hydroxyl orC₁-C₆-alkyl;

 where

R¹¹ and R¹² together with the carbon to which they are attached may alsoform a carbonyl group.

Most preference is also given to the compounds in which hex is a radicalof the formula IIa.

TABLE A Particularly preferred combinations of R¹, R² and R³ R³ R¹ R² 1H CH₃ CH₃ 2 F CH₃ CH₃ 3 Cl CH₃ CH₃ 4 Br CH₃ CH₃ 5 OH CH₃ CH₃ 6 SH CH₃CH₃ 7 NH₂ CH₃ CH₃ 8 CN CH₃ CH₃ 9 NO₂ CH₃ CH₃ 10 SCN CH₃ CH₃ 11 NH—NH₂CH₃ CH₃ 12 CH₃ CH₃ CH₃ 13 C₂H₅ CH₃ CH₃ 14 n-C₃H₇ CH₃ CH₃ 15 i-C₃H₇ CH₃CH₃ 16 n-C₄H₉ CH₃ CH₃ 17 s-C₄H₉ CH₃ CH₃ 18 i-C₄H₉ CH₃ CH₃ 19 t-C₄H₉ CH₃CH₃ 20 CH₂Cl CH₃ CH₃ 21 CHCl₂ CH₃ CH₃ 22 CCl₃ CH₃ CH₃ 23 CH₂F CH₃ CH₃ 24CHF₂ CH₃ CH₃ 25 CF₃ CH₃ CH₃ 62 CH₂CF₃ CH₃ CH₃ 27 CH₂OCH₃ CH₃ CH₃ 28CH₂OCH₂CH₃ CH₃ CH₃ 29 CH₂NH₂ CH₃ CH₃ 30 OCH₃ CH₃ CH₃ 31 OC₂H₅ CH₃ CH₃ 32O-n-C₃H₇ CH₃ CH₃ 33 O-i-C₃H₇ CH₃ CH₃ 34 O-n-C₄H₉ CH₃ CH₃ 35 O-s-C₄H₉ CH₃CH₃ 36 O-i-C₄H₉ CH₃ CH₃ 37 O-t-C₄H₉ CH₃ CH₃ 38 OCHF₂ CH₃ CH₃ 39 OCF₃ CH₃CH₃ 40 OCH₂CF₃ CH₃ CH₃ 41 OCH₂OCH₃ CH₃ CH₃ 42 SCH₃ CH₃ CH₃ 43 SC₂H₅ CH₃CH₃ 44 S-n-C₃H₇ CH₃ CH₃ 45 S-i-C₃H₇ CH₃ CH₃ 46 S-n-C₄H₉ CH₃ CH₃ 47S-s-C₄H₉ CH₃ CH₃ 48 S-i-C₄H₉ CH₃ CH₃ 49 S-t-C₄H₉ CH₃ CH₃ 50 SCHF₂ CH₃CH₃ 51 SCF₃ CH₃ CH₃ 52 SCH₂CF₃ CH₃ CH₃ 53 SCH₂OCH₃ CH₃ CH₃ 54 NHCH₃ CH₃CH₃ 55 NHC₂H₅ CH₃ CH₃ 56 NH-phenyl CH₃ CH₃ 57 N(CH₃)₂ CH₃ CH₃ 58N(CH₂CH₃)₂ CH₃ CH₃ 59 N(phenyl)₂ CH₃ CH₃ 60 (CH₂)₂COCH₃ CH₃ CH₃ 61phenyl CH₃ CH₃ 62 2-F-phenyl CH₃ CH₃ 63 3-F-phenyl CH₃ CH₃ 64 4-F-phenylCH₃ CH₃ 65 2-Cl-phenyl CH₃ CH₃ 66 3-Cl-phenyl CH₃ CH₃ 67 4-Cl-phenyl CH₃CH₃ 68 2-OH-phenyl CH₃ CH₃ 69 3-OH-phenyl CH₃ CH₃ 70 4-OH-phenyl CH₃ CH₃71 2-OCH₃-phenyl CH₃ CH₃ 72 3-OCH₃-phenyl CH₃ CH₃ 73 4-OCH₃-phenyl CH₃CH₃ 74 2-OCF₃-phenyl CH₃ CH₃ 75 3-OCF₃-phenyl CH₃ CH₃ 76 4-OCF₃-phenylCH₃ CH₃ 77 2-OCHF₂-phenyl CH₃ CH₃ 78 3-OCHF₂-phenyl CH₃ CH₃ 794-OCHF₂-phenyl CH₃ CH₃ 80 2-CF₃-phenyl CH₃ CH₃ 81 3-CF₃-phenyl CH₃ CH₃82 4-CF₃-phenyl CH₃ CH₃ 83 2-CH₃-phenyl CH₃ CH₃ 84 3-CH₃-phenyl CH₃ CH₃85 4-CH₃-phenyl CH₃ CH₃ 86 2-NO₂-phenyl CH₃ CH₃ 87 3-NO₂-phenyl CH₃ CH₃88 4-NO₂-phenyl CH₃ CH₃ 89 2-pyridyl CH₃ CH₃ 90 3-pyridyl CH₃ CH₃ 914-pyridyl CH₃ CH₃ 92 3′-CH₃-2-pyridyl CH₃ CH₃ 93 4′-CH₃-2-pyridyl CH₃CH₃ 94 5′-CH₃-2-pyridyl CH₃ CH₃ 95 6′-CH₃-2-pyridyl CH₃ CH₃ 962′-CH₃-3-pyridyl CH₃ CH₃ 97 4′-CH₃-3-pyridyl CH₃ CH₃ 98 5′-CH₃-3-pyridylCH₃ CH₃ 99 6′-CH₃-3-pyridyl CH₃ CH₃ 100 2′-CH₃-4-pyridyl CH₃ CH₃ 1013′-CH₃-4-pyridyl CH₃ CH₃ 102 3′-Cl-2-pyridyl CH₃ CH₃ 103 4′-Cl-2-pyridylCH₃ CH₃ 104 5′-Cl-2-pyridyl CH₃ CH₃ 105 6′-Cl-2-pyridyl CH₃ CH₃ 1062′-Cl-3-pyridyl CH₃ CH₃ 107 4′-Cl-3-pyridyl CH₃ CH₃ 108 5′-Cl-3-pyridylCH₃ CH₃ 109 6′-Cl-3-pyridyl CH₃ CH₃ 110 2′-Cl-4-pyridyl CH₃ CH₃ 1113′-Cl-4-pyridyl CH₃ CH₃ 112 cyclohexylamino CH₃ CH₃ 113 cyclopentylaminoCH₃ CH₃ 114 morpholino CH₃ CH₃ 115 CO₂H CH₃ CH₃ 116 CO₂CH₃ CH₃ CH₃ 117CO₂C₂H₅ CH₃ CH₃ 118 CO₂-n-C₃H₇ CH₃ CH₃ 119 CO₂-i-C₃H₇ CH₃ CH₃ 120CO₂-n-C₄H₉ CH₃ CH₃ 121 CO₂-s-C₄H₉ CH₃ CH₃ 122 CO₂-i-C₄H₉ CH₃ CH₃ 123CO₂-t-C₄H₉ CH₃ CH₃ 124 CO₂-Ph CH₃ CH₃ 125 CO₂-3-pyridyl CH₃ CH₃ 126CONHCH₃ CH₃ CH₃ 127 CONHC₂H₅ CH₃ CH₃ 128 CONHPh CH₃ CH₃ 129 CON(CH₃)₂CH₃ CH₃ 130 CON(CH₂CH₃)₂ CH₃ CH₃ 131 CON(phenyl)₂ CH₃ CH₃ 132 H OCH₃ CH₃133 F OCH₃ CH₃ 134 Cl OCH₃ CH₃ 135 Br OCH₃ CH₃ 136 OH OCH₃ CH₃ 137 SHOCH₃ CH₃ 138 NH₂ OCH₃ CH₃ 139 CN OCH₃ CH₃ 140 NO₂ OCH₃ CH₃ 141 SCN OCH₃CH₃ 142 NH—NH₂ OCH₃ CH₃ 143 CH₃ OCH₃ CH₃ 144 C₂H₅ OCH₃ CH₃ 145 n-C₃H₇OCH₃ CH₃ 146 i-C₃H₇ OCH₃ CH₃ 147 n-C₄H₉ OCH₃ CH₃ 148 s-C₄H₉ OCH₃ CH₃ 149i-C₄H₉ OCH₃ CH₃ 150 t-C₄H₉ OCH₃ CH₃ 151 CH₂Cl OCH₃ CH₃ 152 CHCl₂ OCH₃CH₃ 153 CCl₃ OCH₃ CH₃ 154 CH₂F OCH₃ CH₃ 155 CHF₂ OCH₃ CH₃ 156 CF₃ OCH₃CH₃ 157 CH₂CF₃ OCH₃ CH₃ 158 CH₂OCH₃ OCH₃ CH₃ 159 CH₂OCH₂CH₃ OCH₃ CH₃ 160CH₂NH₂ OCH₃ CH₃ 161 OCH₃ OCH₃ CH₃ 162 OC₂H₅ OCH₃ CH₃ 163 O-n-C₃H₇ OCH₃CH₃ 164 O-i-C₃H₇ OCH₃ CH₃ 165 O-n-C₄H₉ OCH₃ CH₃ 166 O-s-C₄H₉ OCH₃ CH₃167 O-i-C₄H₉ OCH₃ CH₃ 168 O-t-C₄H₉ OCH₃ CH₃ 169 OCHF₂ OCH₃ CH₃ 170 OCF₃OCH₃ CH₃ 171 OCH₂CF₃ OCH₃ CH₃ 172 OCH₂OCH₃ OCH₃ CH₃ 173 SCH₃ OCH₃ CH₃174 SC₂H₅ OCH₃ CH₃ 175 S-n-C₃H₇ OCH₃ CH₃ 176 S-i-C₃H₇ OCH₃ CH₃ 177S-n-C₄H₉ OCH₃ CH₃ 178 S-s-C₄H₉ OCH₃ CH₃ 179 S-i-C₄H₉ OCH₃ CH₃ 180S-t-C₄H₉ OCH₃ CH₃ 181 SCHF₂ OCH₃ CH₃ 182 SCF₃ OCH₃ CH₃ 183 SCH₂CF₃ OCH₃CH₃ 184 SCH₂OCH₃ OCH₃ CH₃ 185 NHCH₃ OCH₃ CH₃ 186 NHC₂H₅ OCH₃ CH₃ 187NHphenyl OCH₃ CH₃ 188 N(CH₃)₂ OCH₃ CH₃ 189 N(CH₂CH₃)₂ OCH₃ CH₃ 190N(phenyl)₂ OCH₃ CH₃ 191 (CH₂)₂COCH₃ OCH₃ CH₃ 192 phenyl OCH₃ CH₃ 1932-F-phenyl OCH₃ CH₃ 194 3-F-phenyl OCH₃ CH₃ 195 4-F-phenyl OCH₃ CH₃ 1962-Cl-phenyl OCH₃ CH₃ 197 3-Cl-phenyl OCH₃ CH₃ 198 4-Cl-phenyl OCH₃ CH₃199 2-OH-phenyl OCH₃ CH₃ 200 3-OH-phenyl OCH₃ CH₃ 201 4-OH-phenyl OCH₃CH₃ 202 2-OCH₃-phenyl OCH₃ CH₃ 203 3-OCH₃-phenyl OCH₃ CH₃ 2044-OCH₃-phenyl OCH₃ CH₃ 205 2-OCF₃-phenyl OCH₃ CH₃ 206 3-OCF₃-phenyl OCH₃CH₃ 207 4-OCF₃-phenyl OCH₃ CH₃ 208 2-OCHF₂-phenyl OCH₃ CH₃ 2093-OCHF₂-phenyl OCH₃ CH₃ 210 4-OCHF₂-phenyl OCH₃ CH₃ 211 2-CF₃-phenylOCH₃ CH₃ 212 3-CF₃-phenyl OCH₃ CH₃ 213 4-CF₃-phenyl OCH₃ CH₃ 2142-CH₃-phenyl OCH₃ CH₃ 215 3-CH₃-phenyl OCH₃ CH₃ 216 4-CH₃-phenyl OCH₃CH₃ 217 2-NO₂-phenyl OCH₃ CH₃ 218 3-NO₂-phenyl OCH₃ CH₃ 219 4-NO₂-phenylOCH₃ CH₃ 220 2-pyridyl OCH₃ CH₃ 221 3-pyridyl OCH₃ CH₃ 222 4-pyridylOCH₃ CH₃ 223 3′-CH₃-2-pyridyl OCH₃ CH₃ 224 4′-CH₃-2-pyridyl OCH₃ CH₃ 2255′-CH₃-2-pyridyl OCH₃ CH₃ 226 6′-CH₃-2-pyridyl OCH₃ CH₃ 2272′-CH₃-3-pyridyl OCH₃ CH₃ 228 4′-CH₃-3-pyridyl OCH₃ CH₃ 2295′-CH₃-3-pyridyl OCH₃ CH₃ 230 6′-CH₃-3-pyridyl OCH₃ CH₃ 2312′-CH₃-4-pyridyl OCH₃ CH₃ 232 3′-CH₃-4-pyridyl OCH₃ CH₃ 2333′-Cl-2-pyridyl OCH₃ CH₃ 234 4′-Cl-2-pyridyl OCH₃ CH₃ 2355′-Cl-2-pyridyl OCH₃ CH₃ 236 6′-Cl-2-pyridyl OCH₃ CH₃ 2372′-Cl-3-pyridyl OCH₃ CH₃ 238 4′-Cl-3-pyridyl OCH₃ CH₃ 2395′-Cl-3-pyridyl OCH₃ CH₃ 240 6′-Cl-3-pyridyl OCH₃ CH₃ 2412′-Cl-4-pyridyl OCH₃ CH₃ 242 3′-Cl-4-pyridyl OCH₃ CH₃ 243cyclohexylamino OCH₃ CH₃ 244 cyclopentylamino OCH₃ CH₃ 245 morpholinoOCH₃ CH₃ 246 CO₂H OCH₃ CH₃ 247 CO₂CH₃ OCH₃ CH₃ 248 CO₂C₂H₅ OCH₃ CH₃ 249CO₂-n-C₃H₇ OCH₃ CH₃ 250 CO₂-i-C₃H₇ OCH₃ CH₃ 251 CO₂-n-C₄H₉ OCH₃ CH₃ 252CO₂-s-C₄H₉ OCH₃ CH₃ 253 CO₂-i-C₄H₉ OCH₃ CH₃ 254 CO₂-t-C₄H₉ OCH₃ CH₃ 255CO₂-Ph OCH₃ CH₃ 256 CO₂-3-pyridyl OCH₃ CH₃ 257 CONHCH₃ OCH₃ CH₃ 258CONHC₂H₅ OCH₃ CH₃ 259 CONHphenyl OCH₃ CH₃ 260 CON(CH₃)₂ OCH₃ CH₃ 261CON(CH₂CH₃)₂ OCH₃ CH₃ 262 CON(phenyl)₂ OCH₃ CH₃ 263 H Cl CH₃ 264 F ClCH₃ 265 Cl Cl CH₃ 266 Br Cl CH₃ 267 OH Cl CH₃ 268 SH Cl CH₃ 269 NH₂ ClCH₃ 270 CN Cl CH₃ 271 NO₂ Cl CH₃ 272 SCN Cl CH₃ 273 NH—NH₂ Cl CH₃ 274CH₃ Cl CH₃ 275 C₂H₅ Cl CH₃ 276 n-C₃H₇ Cl CH₃ 277 i-C₃H₇ Cl CH₃ 278n-C₄H₉ Cl CH₃ 279 s-C₄H₉ Cl CH₃ 280 i-C₄H₉ Cl CH₃ 281 t-C₄H₉ Cl CH₃ 282CH₂Cl Cl CH₃ 283 CHCl₂ Cl CH₃ 284 CCl₃ Cl CH₃ 285 CH₂F Cl CH₃ 286 CHF₂Cl CH₃ 287 CF₃ Cl CH₃ 288 CH₂CF₃ Cl CH₃ 289 CH₂OCH₃ Cl CH₃ 290CH₂OCH₂CH₃ Cl CH₃ 291 CH₂NH₂ Cl CH₃ 292 OCH₃ Cl CH₃ 293 OC₂H₅ Cl CH₃ 294O-n-C₃H₇ Cl CH₃ 295 O-i-C₃H₇ Cl CH₃ 296 O-n-C₄H₉ Cl CH₃ 297 O-s-C₄H₉ ClCH₃ 298 O-i-C₄H₉ Cl CH₃ 299 O-t-C₄H₉ Cl CH₃ 300 OCHF₂ Cl CH₃ 301 OCF₃ ClCH₃ 302 OCH₂CF₃ Cl CH₃ 303 OCH₂OCH₃ Cl CH₃ 304 SCH₃ Cl CH₃ 305 SC₂H₅ ClCH₃ 306 S-n-C₃H₇ Cl CH₃ 307 S-i-C₃H₇ Cl CH₃ 308 S-n-C₄H₉ Cl CH₃ 309S-s-C₄H₉ Cl CH₃ 310 S-i-C₄H₉ Cl CH₃ 311 S-t-C₄H₉ Cl CH₃ 312 SCHF₂ Cl CH₃313 SCF₃ Cl CH₃ 314 SCH₂CF₃ Cl CH₃ 315 SCH₂OCH₃ Cl CH₃ 316 NHCH₃ Cl CH₃317 NHC₂H₅ Cl CH₃ 318 NH-phenyl Cl CH₃ 319 N(CH₃)₂ Cl CH₃ 320 N(CH₂CH₃)₂Cl CH₃ 321 N(phenyl)₂ Cl CH₃ 322 (CH₂)₂COCH₃ Cl CH₃ 323 phenyl Cl CH₃324 2-F-phenyl Cl CH₃ 325 3-F-phenyl Cl CH₃ 362 4-F-phenyl Cl CH₃ 3272-Cl-phenyl Cl CH₃ 328 3-Cl-phenyl Cl CH₃ 329 4-Cl-phenyl Cl CH₃ 3302-OH-phenyl Cl CH₃ 331 3-OH-phenyl Cl CH₃ 332 4-OH-phenyl Cl CH₃ 3332-OCH₃-phenyl Cl CH₃ 334 3-OCH₃-phenyl Cl CH₃ 335 4-OCH₃-phenyl Cl CH₃336 2-OCF₃-phenyl Cl CH₃ 337 3-OCF₃-phenyl Cl CH₃ 338 4-OCF₃-phenyl ClCH₃ 339 2-OCHF₂-phenyl Cl CH₃ 340 3-OCHF₂-phenyl Cl CH₃ 3414-OCHF₂-phenyl Cl CH₃ 342 2-CF₃-phenyl Cl CH₃ 343 3-CF₃-phenyl Cl CH₃344 4-CF₃-phenyl Cl CH₃ 345 2-CH₃-phenyl Cl CH₃ 346 3-CH₃-phenyl Cl CH₃347 4-CH₃-phenyl Cl CH₃ 348 2-NO₂-phenyl Cl CH₃ 349 3-NO₂-phenyl Cl CH₃350 4-NO₂-phenyl Cl CH₃ 351 2-pyridyl Cl CH₃ 352 3-pyridyl Cl CH₃ 3534-pyridyl Cl CH₃ 354 3′-CH₃-2-pyridyl Cl CH₃ 355 4′-CH₃-2-pyridyl Cl CH₃356 5′-CH₃-2-pyridyl Cl CH₃ 357 6′-CH₃-2-pyridyl Cl CH₃ 3582′-CH₃-3-pyridyl Cl CH₃ 359 4′-CH₃-3-pyridyl Cl CH₃ 360 5′-CH₃-3-pyridylCl CH₃ 361 6′-CH₃-3-pyridyl Cl CH₃ 362 2′-CH₃-4-pyridyl Cl CH₃ 3633′-CH₃-4-pyridyl Cl CH₃ 364 3′-Cl-2-pyridyl Cl CH₃ 365 4′-Cl-2-pyridylCl CH₃ 366 5′-Cl-2-pyridyl Cl CH₃ 367 6′-Cl-2-pyridyl Cl CH₃ 3682′-Cl-3-pyridyl Cl CH₃ 369 4′-Cl-3-pyridyl Cl CH₃ 370 5′-Cl-3-pyridyl ClCH₃ 371 6′-Cl-3-pyridyl Cl CH₃ 372 2′-Cl-4-pyridyl Cl CH₃ 3733′-Cl-4-pyridyl Cl CH₃ 374 cyclohexylamino Cl CH₃ 375 cyclopentylaminoCl CH₃ 376 morpholino Cl CH₃ 377 CO₂H Cl CH₃ 378 CO₂CH₃ Cl CH₃ 379CO₂C₂H₅ Cl CH₃ 380 CO₂-n-C₃H₇ Cl CH₃ 381 CO₂-i-C₃H₇ Cl CH₃ 382CO₂-n-C₄H₉ Cl CH₃ 383 CO₂-s-C₄H₉ Cl CH₃ 384 CO₂-i-C₄H₉ Cl CH₃ 385CO₂-t-C₄H₉ Cl CH₃ 386 CO₂-phenyl Cl CH₃ 387 CO₂-3-pyridyl Cl CH₃ 388CONHCH₃ Cl CH₃ 389 CONHC₂H₅ Cl CH₃ 390 CONH-phenyl Cl CH₃ 391 CON(CH₃)₂Cl CH₃ 392 CON(CH₂CH₃)₂ Cl CH₃ 393 CON(phenyl)₂ Cl CH₃ 394 H CH₃ H 394 FCH₃ H 396 Cl CH₃ H 397 Br CH₃ H 398 OH CH₃ H 399 SH CH₃ H 400 NH₂ CH₃ H401 CN CH₃ H 402 NO₂ CH₃ H 403 SCN CH₃ H 404 NH—NH₂ CH₃ H 405 CH₃ CH₃ H406 C₂H₅ CH₃ H 407 n-C₃H₇ CH₃ H 408 i-C₃H₇ CH₃ H 049 n-C₄H₉ CH₃ H 410s-C₄H₉ CH₃ H 411 i-C₄H₉ CH₃ H 412 t-C₄H₉ CH₃ H 413 CH₂Cl CH₃ H 414 CHCl₂CH₃ H 415 CCl₃ CH₃ H 416 CH₂F CH₃ H 417 CHF₂ CH₃ H 418 CF₃ CH₃ H 419CH₂CF₃ CH₃ H 420 CH₂OCH₃ CH₃ H 421 CH₂OCH₂CH₃ CH₃ H 422 CH₂NH₂ CH₃ H 423OCH₃ CH₃ H 424 OC₂H₅ CH₃ H 425 O-n-C₃H₇ CH₃ H 462 O-i-C₃H₇ CH₃ H 427O-n-C₄H₉ CH₃ H 428 O-s-C₄H₉ CH₃ H 429 O-i-C₄H₉ CH₃ H 430 O-t-C₄H₉ CH₃ H431 OCHF₂ CH₃ H 432 OCF₃ CH₃ H 433 OCH₂CF₃ CH₃ H 434 OCH₂OCH₃ CH₃ H 435SCH₃ CH₃ H 436 SC₂H₅ CH₃ H 437 S-n-C₃H₇ CH₃ H 438 S-i-C₃H₇ CH₃ H 439S-n-C₄H₉ CH₃ H 440 S-s-C₄H₉ CH₃ H 441 S-i-C₄H₉ CH₃ H 442 S-t-C₄H₉ CH₃ H443 SCHF₂ CH₃ H 444 SCF₃ CH₃ H 445 SCH₂CF₃ CH₃ H 446 SCH₂OCH₃ CH₃ H 447NHCH₃ CH₃ H 448 NHC₂H₅ CH₃ H 449 NH-phenyl CH₃ H 450 N(CH₃)₂ CH₃ H 451N(CH₂CH₃)₂ CH₃ H 452 N(phenyl)₂ CH₃ H 453 (CH₂)₂COCH₃ CH₃ H 454 phenylCH₃ H 455 2-F-phenyl CH₃ H 456 3-F-phenyl CH₃ H 457 4-F-phenyl CH₃ H 4582-Cl-phenyl CH₃ H 459 3-Cl-phenyl CH₃ H 460 4-Cl-phenyl CH₃ H 4612-OH-phenyl CH₃ H 462 3-OH-phenyl CH₃ H 463 4-OH-phenyl CH₃ H 4642-OCH₃-phenyl CH₃ H 465 3-OCH₃-phenyl CH₃ H 466 4-OCH₃-phenyl CH₃ H 4672-OCF₃-phenyl CH₃ H 468 3-OCF₃-phenyl CH₃ H 469 4-OCF₃-phenyl CH₃ H 4702-OCHF₂-phenyl CH₃ H 471 3-OCHF₂-phenyl CH₃ H 472 4-OCHF₂-phenyl CH₃ H473 2-CF₃-phenyl CH₃ H 474 3-CF₃-phenyl CH₃ H 475 4-CF₃-phenyl CH₃ H 4762-CH₃-phenyl CH₃ H 477 3-CH₃-phenyl CH₃ H 478 4-CH₃-phenyl CH₃ H 4792-NO₂-phenyl CH₃ H 480 3-NO₂-phenyl CH₃ H 481 4-NO₂-phenyl CH₃ H 4822-pyridyl CH₃ H 483 3-pyridyl CH₃ H 484 4-pyridyl CH₃ H 4853′-CH₃-2-pyridyl CH₃ H 486 4′-CH₃-2-pyridyl CH₃ H 487 5′-CH₃-2-pyridylCH₃ H 488 6′-CH₃-2-pyridyl CH₃ H 489 2′-CH₃-3-pyridyl CH₃ H 4904′-CH₃-3-pyridyl CH₃ H 491 5′-CH₃-3-pyridyl CH₃ H 492 6′-CH₃-3-pyridylCH₃ H 493 2′-CH₃-4-pyridyl CH₃ H 494 3′-CH₃-4-pyridyl CH₃ H 4953′-Cl-2-pyridyl CH₃ H 496 4′-Cl-2-pyridyl CH₃ H 497 5′-Cl-2-pyridyl CH₃H 498 6′-Cl-2-pyridyl CH₃ H 499 2′-Cl-3-pyridyl CH₃ H 5004′-Cl-3-pyridyl CH₃ H 501 5′-Cl-3-pyridyl CH₃ H 502 6′-Cl-3-pyridyl CH₃H 503 2′-Cl-4-pyridyl CH₃ H 504 3′-Cl-4-pyridyl CH₃ H 505cyclohexylamino CH₃ H 506 cyclopentylamino CH₃ H 507 morpholino CH₃ H508 CO₂H CH₃ H 509 CO₂CH₃ CH₃ H 510 CO₂C₂H₅ CH₃ H 511 CO₂-n-C₃H₇ CH₃ H512 CO₂-i-C₃H₇ CH₃ H 513 CO₂-n-C₄H₉ CH₃ H 514 CO₂-s-C₄H₉ CH₃ H 515CO₂-i-C₄H₉ CH₃ H 516 CO₂-t-C₄H₉ CH₃ H 517 CO₂-Ph CH₃ H 518 CO₂-3-pyridylCH₃ H 519 CONHCH₃ CH₃ H 520 CONHC₂H₅ CH₃ H 521 CONH-phenyl CH₃ H 522CON(CH₃)₂ CH₃ H 523 CON(CH₂CH₃)₂ CH₃ H 524 CON(phenyl)₂ CH₃ H 525 H OCH₃H 526 F OCH₃ H 527 Cl OCH₃ H 528 Br OCH₃ H 529 OH OCH₃ H 530 SH OCH₃ H531 NH₂ OCH₃ H 532 CN OCH₃ H 533 NO₂ OCH₃ H 534 SCN OCH₃ H 535 NH—NH₂OCH₃ H 536 CH₃ OCH₃ H 537 C₂H₅ OCH₃ H 538 n-C₃H₇ OCH₃ H 539 i-C₃H₇ OCH₃H 540 n-C₄H₉ OCH₃ H 541 s-C₄H₉ OCH₃ H 542 i-C₄H₉ OCH₃ H 543 t-C₄H₉ OCH₃H 544 CH₂Cl OCH₃ H 545 CHCl₂ OCH₃ H 546 CCl₃ OCH₃ H 547 CH₂F OCH₃ H 548CHF₂ OCH₃ H 549 CF₃ OCH₃ H 550 CH₂CF₃ OCH₃ H 551 CH₂OCH₃ OCH₃ H 552CH₂OCH₂CH₃ OCH₃ H 553 CH₂NH₂ OCH₃ H 554 OCH₃ OCH₃ H 555 OC₂H₅ OCH₃ H 556O-n-C₃H₇ OCH₃ H 557 O-i-C₃H₇ OCH₃ H 558 O-n-C₄H₉ OCH₃ H 559 O-s-C₄H₉OCH₃ H 560 O-i-C₄H₉ OCH₃ H 561 O-t-C₄H₉ OCH₃ H 562 OCHF₂ OCH₃ H 563 OCF₃OCH₃ H 564 OCH₂CF₃ OCH₃ H 565 OCH₂OCH₃ OCH₃ H 566 SCH₃ OCH₃ H 567 SC₂H₅OCH₃ H 568 S-n-C₃H₇ OCH₃ H 569 S-i-C₃H₇ OCH₃ H 570 S-n-C₄H₉ OCH₃ H 571S-s-C₄H₉ OCH₃ H 572 S-i-C₄H₉ OCH₃ H 573 S-t-C₄H₉ OCH₃ H 574 SCHF₂ OCH₃ H575 SCF₃ OCH₃ H 576 SCH₂CF₃ OCH₃ H 577 SCH₂OCH₃ OCH₃ H 578 NHCH₃ OCH₃ H579 NHC₂H₅ OCH₃ H 580 NHPh OCH₃ H 581 N(CH₃)₂ OCH₃ H 582 N(CH₂CH₃)₂ OCH₃H 583 N(phenyl)₂ OCH₃ H 584 (CH₂)₂COCH₃ OCH₃ H 585 phenyl OCH₃ H 5862-F-phenyl OCH₃ H 587 3-F-phenyl OCH₃ H 588 4-F-phenyl OCH₃ H 5892-Cl-phenyl OCH₃ H 590 3-Cl-phenyl OCH₃ H 591 4-Cl-phenyl OCH₃ H 5922-OH-phenyl OCH₃ H 593 3-OH-phenyl OCH₃ H 594 4-OH-phenyl OCH₃ H 5952-OCH₃-phenyl OCH₃ H 596 3-OCH₃-phenyl OCH₃ H 597 4-OCH₃-phenyl OCH₃ H598 2-OCF₃-phenyl OCH₃ H 599 3-OCF₃-phenyl OCH₃ H 600 4-OCF₃-phenyl OCH₃H 601 2-OCHF₂-phenyl OCH₃ H 602 3-OCHF₂-phenyl OCH₃ H 603 4-OCHF₂-phenylOCH₃ H 604 2-CF₃-phenyl OCH₃ H 605 3-CF₃-phenyl OCH₃ H 606 4-CF₃-phenylOCH₃ H 607 2-CH₃-phenyl OCH₃ H 608 3-CH₃-phenyl OCH₃ H 609 4-CH₃-phenylOCH₃ H 610 2-NO₂-phenyl OCH₃ H 611 3-NO₂-phenyl OCH₃ H 612 4-NO₂-phenylOCH₃ H 613 2-pyridyl OCH₃ H 614 3-pyridyl OCH₃ H 615 4-pyridyl OCH₃ H616 3′-CH₃-2-pyridyl OCH₃ H 617 4′-CH₃-2-pyridyl OCH₃ H 6185′-CH₃-2-pyridyl OCH₃ H 619 6′-CH₃-2-pyridyl OCH₃ H 620 2′-CH₃-3-pyridylOCH₃ H 621 4′-CH₃-3-pyridyl OCH₃ H 622 5′-CH₃-3-pyridyl OCH₃ H 6236′-CH₃-3-pyridyl OCH₃ H 624 2′-CH₃-4-pyridyl OCH₃ H 625 3′-CH₃-4-pyridylOCH₃ H 626 3′-Cl-2-pyridyl OCH₃ H 627 4′-Cl-2-pyridyl OCH₃ H 6285′-Cl-2-pyridyl OCH₃ H 629 6′-Cl-2-pyridyl OCH₃ H 630 2′-Cl-3-pyridylOCH₃ H 631 4′-Cl-3-pyridyl OCH₃ H 632 5′-Cl-3-pyridyl OCH₃ H 6336′-Cl-3-pyridyl OCH₃ H 634 2′-Cl-4-pyridyl OCH₃ H 635 3′-Cl-4-pyridylOCH₃ H 636 cyclohexylamino OCH₃ H 637 cyclopentylamino OCH₃ H 638morpholino OCH₃ H 639 CO₂H OCH₃ H 640 CO₂CH₃ OCH₃ H 641 CO₂C₂H₅ OCH₃ H642 CO₂-n-C₃H₇ OCH₃ H 643 CO₂-i-C₃H₇ OCH₃ H 644 CO₂-n-C₄H₉ OCH₃ H 645CO₂-s-C₄H₉ OCH₃ H 646 CO₂-i-C₄H₉ OCH₃ H 647 CO₂-t-C₄H₉ OCH₃ H 648 CO₂-PhOCH₃ H 649 CO₂-3-pyridyl OCH₃ H 650 CONHCH₃ OCH₃ H 651 CONHC₂H₅ OCH₃ H652 CONH-phenyl OCH₃ H 653 CON(CH₃)₂ OCH₃ H 654 CON(CH₂CH₃)₂ OCH₃ H 655CON(phenyl)₂ OCH₃ H 656 H Cl H 657 F Cl H 658 Cl Cl H 659 Br Cl H 660 OHCl H 661 SH Cl H 662 NH₂ Cl H 663 CN Cl H 664 NO₂ Cl H 665 SCN Cl H 666NH—NH₂ Cl H 667 CH₃ Cl H 668 C₂H₅ Cl H 669 n-C₃H₇ Cl H 670 i-C₃H₇ Cl H671 n-C₄H₉ Cl H 672 s-C₄H₉ Cl H 673 i-C₄H₉ Cl H 674 t-C₄H₉ Cl H 675CH₂Cl Cl H 676 CHCl₂ Cl H 677 CCl₃ Cl H 678 CH₂F Cl H 679 CHF₂ Cl H 680CF₃ Cl H 681 CH₂CF₃ Cl H 682 CH₂OCH₃ Cl H 683 CH₂OCH₂CH₃ Cl H 684 CH₂NH₂Cl H 685 OCH₃ Cl H 686 OC₂H₅ Cl H 687 O-n-C₃H₇ Cl H 688 O-i-C₃H₇ Cl H689 O-n-C₄H₉ Cl H 690 O-s-C₄H₉ Cl H 691 O-i-C₄H₉ Cl H 692 O-t-C₄H₉ Cl H693 OCHF₂ Cl H 694 OCF₃ Cl H 695 OCH₂CF₃ Cl H 696 OCH₂OCH₃ Cl H 697 SCH₃Cl H 698 SC₂H₅ Cl H 699 S-n-C₃H₇ Cl H 700 S-i-C₃H₇ Cl H 701 S-n-C₄H₉ ClH 702 S-s-C₄H₉ Cl H 703 S-i-C₄H₉ Cl H 704 S-t-C₄H₉ Cl H 705 SCHF₂ Cl H706 SCF₃ Cl H 707 SCH₂CF₃ Cl H 708 SCH₂OCH₃ Cl H 709 NHCH₃ Cl H 710NHC₂H₅ Cl H 711 NHPh Cl H 712 N(CH₃)₂ Cl H 713 N(CH₂CH₃)₂ Cl H 714N(phenyl)₂ Cl H 715 (CH₂)₂COCH₃ Cl H 716 phenyl Cl H 717 2-F-phenyl Cl H718 3-F-phenyl Cl H 719 4-F-phenyl Cl H 720 2-Cl-phenyl Cl H 7213-Cl-phenyl Cl H 722 4-Cl-phenyl Cl H 723 2-OH-phenyl Cl H 7243-OH-phenyl Cl H 725 4-OH-phenyl Cl H 726 2-OCH₃-phenyl Cl H 7273-OCH₃-phenyl Cl H 728 4-OCH₃-phenyl Cl H 729 2-OCF₃-phenyl Cl H 7303-OCF₃-phenyl Cl H 731 4-OCF₃-phenyl Cl H 732 2-OCHF₂-phenyl Cl H 7333-OCHF₂-phenyl Cl H 734 4-OCHF₂-phenyl Cl H 735 2-CF₃-phenyl Cl H 7363-CF₃-phenyl Cl H 737 4-CF₃-phenyl Cl H 738 2-CH₃-phenyl Cl H 7393-CH₃-phenyl Cl H 740 4-CH₃-phenyl Cl H 741 2-NO₂-phenyl Cl H 7423-NO₂-phenyl Cl H 743 4-NO₂-phenyl Cl H 744 2-pyridyl Cl H 745 3-pyridylCl H 746 4-pyridyl Cl H 747 3′-CH₃-2-pyridyl Cl H 748 4′-CH₃-2-pyridylCl H 749 5′-CH₃-2-pyridyl Cl H 750 6′-CH₃-2-pyridyl Cl H 7512′-CH₃-3-pyridyl Cl H 752 4′-CH₃-3-pyridyl Cl H 753 5′-CH₃-3-pyridyl ClH 754 6′-CH₃-3-pyridyl Cl H 755 2′-CH₃-4-pyridyl Cl H 7563′-CH₃-4-pyridyl Cl H 757 3′-Cl-2-pyridyl Cl H 758 4′-Cl-2-pyridyl Cl H759 5′-Cl-2-pyridyl Cl H 760 6′-Cl-2-pyridyl Cl H 761 2′-Cl-3-pyridyl ClH 762 4′-Cl-3-pyridyl Cl H 763 5′-Cl-3-pyridyl Cl H 764 6′-Cl-3-pyridylc1 H 765 2′-Cl-4-pyridyl Cl H 766 3′-Cl-4-pyridyl Cl H 767cyclohexylamino Cl H 768 cyclopentylamino Cl H 769 morpholino Cl H 770CO₂H Cl H 771 CO₂CH₃ Cl H 772 CO₂C₂H₅ Cl H 773 CO₂-n-C₃H₇ Cl H 774CO₂-i-C₃H₇ Cl H 775 CO₂-n-C₄H₉ Cl H 776 CO₂-s-C₄H₉ Cl H 777 CO₂-i-C₄H₉Cl H 778 CO₂-t-C₄H₉ Cl H 779 CO₂-phenyl Cl H 780 CO₂-3-pyridyl Cl H 781CONHCH₃ Cl H 782 CONHC₂H₅ Cl H 783 CONH-phenyl Cl H 784 CON(CH₃)₂ Cl H785 CON(CH₂CH₃)₂ Cl H 786 CON(phenyl)₂ Cl H 787 2-fluorophenoxy CH₃ CH₃788 2-fluorophenoxy OCH₃ CH₃ 789 2-fluorophenoxy Cl CH₃ 7902-fluorophenoxy CH₃ H 791 2-fluorophenoxy OCH₃ H 792 2-fluorophenoxy ClH 793 phenoxy CH₃ CH₃ 794 phenoxy OCH₃ CH₃ 795 phenoxy Cl CH₃ 796phenoxy CH₃ H 797 phenoxy OCH₃ H 798 phenoxy Cl H 799 2-methoxyphenoxyCH₃ CH₃ 800 2-methoxyphenoxy OCH₃ CH₃ 801 2-methoxyphenoxy Cl CH₃ 8022-methoxyphenoxy CH₃ H 803 2-methoxyphenoxy OCH₃ H 804 2-methoxyphenoxyCl H 805 cyclopropyl CH₃ CH₃ 806 cyclopropyl OCH₃ CH₃ 807 cyclopropyl ClCH₃ 808 cyclopropyl CH₃ H 809 cyclopropyl OCH₃ H 810 cyclopropyl Cl HHere are some further particular examples: 2-F-phenyl = 2-fluorophenyl2-Cl-phenyl = 2-chlorophenyl 2-OH-phenyl = 2-hydroxyphenyl 2-OCH₃-phenyl= 2-methoxyphenyl 2-OCF₃-phenyl = 2-trifluoromethoxyphenyl2-OCHF₂-phenyl = 2-difluoromethoxyphenyl 2-NO₂-phenyl = 2-nitrophenyl3′-CH₃-2-pyridyl = 3′-methylpyridin-2-yl

Examples of benzothiazol-5-ylcarbonyl derivatives of cyclohexenones(compounds I-1=compounds I where X=C—R³ and Y=S) which are particularlypreferred according to the invention are the compounds listed in Tables1 to 25.

TABLE 1 Compounds I-1a.1 to I-1a.810 I-1a

Compounds of the formula I-1a, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 2 Compounds I-1b.1 to I-1b.810 I-1b

Compounds of the formula I-1b, in which the substituents R¹ R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 3 Compounds I-1c.1 to I-1c.810 I-1c

Compounds of the formula I-1c, in which the substituents R₁, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 4 Compounds I-1d.1 to I-1d.810 I-1d

Compounds of the formula I-1d, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 5 Compounds I-1e.1 to I-1e.810 I-1e

Compounds of the formula I-1e, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 6 Compounds I-1f.1 to I-1f.810 I-1f

Compounds of the formula I-1f, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 7 Compounds I-1g.1 to I-1g.810 I-1g

Compounds of the formula I-1g, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 8 Compounds I-1h.1 to I-1h.810 I-1h

Compounds of the formula I-1h, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 9 Compounds I-1i.1 to I-1i.810 I-1i

Compounds of the formula I-1i, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 10 Compounds I-1k.1 to I-1k.810 I-1k

Compounds of the formula I-1k, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 11 Compounds I-1l.1 to I-1l.810 I-1l

Compounds of the formula I-1l, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 12 Compounds I-1m.1 to I-1m.810 I-1m

Compounds of the formula I-1m, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 13 Compounds I-1n.1 to I-1n.810 I-1n

Compounds of the formula I-1n, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 14 Compounds I-1o.1 to I-1o.810 I-1o

Compounds of the formula I-1o, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 15 Compounds I-1p.1 to I-1p.810 I-1p

Compounds of the formula I-1p, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 16 Compounds I-1q.1 to I-1q.810 I-1q

Compounds of the formula I-1q, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 17 Compounds I-1r.1 to I-1r.810 I-1r

Compounds of the formula I-1r, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 18 Compounds I-1s.1 to I-1s.810 I-1s

Compounds of the formula I-1s, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 19 Compounds I-1t.1 to I-1t.810 I-1t

Compounds of the formula I-1t, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 20 Compounds I-1u.1 to I-1u.810 I-1u

Compounds of the formula I-1u, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 21 Compounds I-1v.1 to I-1v.810 I-1v

Compounds of the formula I-1v, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA..

TABLE 22 Compounds I-1w.1 to I-1w.810 I-1w

Compounds of the formula I-1w, in which the substituents R¹, R² and R³for each individual compound correspond in each-case to one row of TableA.

TABLE 23 Compounds I-1x.1 to I-1x.810 I-1x

Compounds of the formula I-1x, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 24 Compounds I-1y.1 to I-1y.810 I-1y

Compounds of the formula I-1y, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 25 Compounds I-1z.1 to I-1z.810 I-1z

Compounds of the formula I-1z, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

Examples of particularly preferred compounds according to the inventionare the benzothiazole S-dioxide compounds I-1′a.1 to I-1′a.810, I-1′b.1to I-1′b.810, . . . I-1′z.1 to I-1′z.810 (compounds I-1′=compounds Iwhere X=C—R³ and Y=SO₂). They differ from the benzothiazole compoundsI-1a.1 to I-1a.810, I-1b.1 to I-1b.810, . . . I-1z.1 to I-1z.810 listedin Tables 1 to 25 in that the heterocyclic sulfur atom is present as anSO₂ group.

Examples of particularly preferred cyclohexenone derivatives ofbenzoxazole-5-carbonyl compounds according to the invention (compoundsI-2 =compounds I where X=C—R³ and Y═O) are the compounds mentioned inTables 26 to 50.

TABLE 26 Compounds I-2a.1 to I-2a.810 I-2a

Compounds of the formula I-2a, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 27 Compounds I-2b.1 to I-2b.810 I-2b

Compounds of the formula I-2b, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 28 Compounds I-2c.1 to I-2c.810 I-2c

Compounds of the formula I-2c, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 29 Compounds I-2d.1 to I-2d.810 I-2d

Compounds of the formula I-2d, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 30 Compounds I-2e.1 to I-2e.810 I-2e

Compounds of the formula I-2e, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 31 Compounds I-2f.1 to I-2f.810 I-2f

Compounds of the formula I-2f, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 32 Compounds I-2g.1 to I-2g.810 I-2g

Compounds of the formula I-2g, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 33 Compounds I-2h.1 to I-2h.810 I-2h

Compounds of the formula I-2h, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 34 Compounds I-2i.1 to I-2i.810 I-2i

Compounds of the formula I-2i, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 35 Compounds I-2k.1 to I-2k.810 I-2k

Compounds of the formula I-2k, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 36 Compounds I-2l.1 to I-2l.810 I-2l

Compounds of the formula I-21, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 37 Compounds I-2m.1 to I-2m.810 I-2m

Compounds of the formula I-2m, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 38 Compounds I-2n.1 to I-2n.810 I-2n

Compounds of the formula I-2n, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 39 Compounds I-2o.1 to I-2o.810 I-2o

Compounds of the formula I-2o, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 40 Compounds I-2p.1 to I-2p.810 I-2p

Compounds of the formula I-2p, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 41 Compounds I-2q.1 to I-2q.810 I-2q

Compounds of the formula I-2q, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 42 Compounds I-2r.1 to I-2r.810 I-2r

Compounds of the formula I-2r, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 43 Compounds I-2s.1 to I-2s.810 I-2s

Compounds of the formula I-2s, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 44 Compounds I-2t.1 to I-2t.810 I-2t

Compounds of the formula I-2t, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 45 Compounds I-2u.1 to I-2u.810 I-2u

Compounds of the formula I-2u, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 46 Compounds I-2v.1 to I-2v.810 I-2v

Compounds of the formula I-2v, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 47 Compounds I-2w.1 to I-2w.810 I-2w

Compounds of the formula I-2w, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 48 Compounds I-2x.1 to I-2x.810 I-2x

Compounds of the formula I-2x, in which the substituents R¹, R² and R³for each individual-compound correspond in each case to one row of TableA.

TABLE 49 Compounds I-2y.1 to I-2y.810 I-2y

Compounds of the formula I-2y, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

TABLE 50 Compounds I-2z.1 to I-2z.810 I-2z

Compounds of the formula I-2z, in which the substituents R¹, R² and R³for each individual compound correspond in each case to one row of TableA.

Particularly preferred combinations of R¹, R², R³ and R⁴ forcyclohexenone derivatives of the formula I according to the inventionwhich are derived from benzimidazole-5-carboxylic acids are listed inTable B below.

TABLE B R³ R¹ R² R⁴  1 CH₃ CH₃ CH₃ H  2 C₂H₅ CH₃ CH₃ H  3 n-C₃H₇ CH₃ CH₃H  4 i-C₃H₇ CH₃ CH₃ H  5 n-C₄H₉ CH₃ CH₃ H  6 s-C₄H₉ CH₃ CH₃ H  7 i-C₄H₉CH₃ CH₃ H  8 t-C₄H₉ CH₃ CH₃ H  9 CH₂Cl CH₃ CH₃ H  10 CHCl₂ CH₃ CH₃ H  11CCl₃ CH₃ CH₃ H  12 CH₂F CH₃ CH₃ H  13 CHF₂ CH₃ CH₃ H  14 CF₃ CH₃ CH₃ H 15 CH₂CF₃ CH₃ CH₃ H  16 CH₂OCH₃ CH₃ CH₃ H  17 CH₂OCH₂CH₃ CH₃ CH₃ H  18CH₂NH₂ CH₃ CH₃ H  19 (CH₂)₂COCH₃ CH₃ CH₃ H  20 phenyl CH₃ CH₃ H  212-F-phenyl CH₃ CH₃ H  22 3-F-phenyl CH₃ CH₃ H  23 4-F-phenyl CH₃ CH₃ H 24 2-Cl-phenyl CH₃ CH₃ H  25 3-Cl-phenyl CH₃ CH₃ H  26 4-Cl-phenyl CH₃CH₃ H  27 2-OH-phenyl CH₃ CH₃ H  28 3-OH-phenyl CH₃ CH₃ H  294-OH-phenyl CH₃ CH₃ H  30 2-OCH₃-phenyl CH₃ CH₃ H  31 3-OCH₃-phenyl CH₃CH₃ H  32 4-OCH₃-phenyl CH₃ CH₃ H  33 2-OCF₃-phenyl CH₃ CH₃ H  343-OCF₃-phenyl CH₃ CH₃ H  35 4-OCF₃-phenyl CH₃ CH₃ H  36 2-OCHF₂-phenylCH₃ CH₃ H  37 3-OCHF₂-phenyl CH₃ CH₃ H  38 4-OCHF₂-phenyl CH₃ CH₃ H  392-CF₃-phenyl CH₃ CH₃ H  40 3-CF₃-phenyl CH₃ CH₃ H  41 4-CF₃-phenyl CH₃CH₃ H  42 2-CH₃-phenyl CH₃ CH₃ H  43 3-CH₃-phenyl CH₃ CH₃ H  444-CH₃-phenyl CH₃ CH₃ H  45 2-NO₂-phenyl CH₃ CH₃ H  46 3-NO₂-phenyl CH₃CH₃ H  47 4-NO₂-phenyl CH₃ CH₃ H  48 2-pyridyl CH₃ CH₃ H  49 3-pyridylCH₃ CH₃ H  50 4-pyridyl CH₃ CH₃ H  51 cyclohexylamino CH₃ CH₃ H  52cyclopentylamino CH₃ CH₃ H  53 H OCH₃ CH₃ H  54 CH₃ OCH₃ CH₃ H  55 C₂H₅OCH₃ CH₃ H  56 n-C₃H₇ OCH₃ CH₃ H  57 i-C₃H₇ OCH₃ CH₃ H  58 n-C₄H₉ OCH₃CH₃ H  59 s-C₄H₉ OCH₃ CH₃ H  60 i-C₄H₉ OCH₃ CH₃ H  61 t-C₄H₉ OCH₃ CH₃ H 62 CH₂Cl OCH₃ CH₃ H  63 CHCl₂ OCH₃ CH₃ H  64 CCl₃ OCH₃ CH₃ H  65 CH₂FOCH₃ CH₃ H  66 CHF₂ OCH₃ CH₃ H  67 CF₃ OCH₃ CH₃ H  68 CH₂CF₃ OCH₃ CH₃ H 69 CH₂OCH₃ OCH₃ CH₃ H  70 CH₂OCH₂CH₃ OCH₃ CH₃ H  71 CH₂NH₂ OCH₃ CH₃ H 72 (CH₂)₂COCH₃ OCH₃ CH₃ H  73 phenyl OCH₃ CH₃ H  74 2-F-phenyl OCH₃ CH₃H  75 3-F-phenyl OCH₃ CH₃ H  76 4-F-phenyl OCH₃ CH₃ H  77 2-Cl-phenylOCH₃ CH₃ H  78 3-Cl-phenyl OCH₃ CH₃ H  79 4-Cl-phenyl OCH₃ CH₃ H  802-OH-phenyl OCH₃ CH₃ H  81 3-OH-phenyl OCH₃ CH₃ H  82 4-OH-phenyl OCH₃CH₃ H  83 2-OCH₃-phenyl OCH₃ CH₃ H  84 3-OCH₃-phenyl OCH₃ CH₃ H  854-OCH₃-phenyl OCH₃ CH₃ H  86 2-OCF₃-phenyl OCH₃ CH₃ H  87 3-OCF₃-phenylOCH₃ CH₃ H  88 4-OCF₃-phenyl OCH₃ CH₃ H  89 2-OCHF₂-phenyl OCH₃ CH₃ H 90 3-OCHF₂-phenyl OCH₃ CH₃ H  91 4-OCHF₂-phenyl OCH₃ CH₃ H  922-CF₃-phenyl OCH₃ CH₃ H  93 3-CF₃-phenyl OCH₃ CH₃ H  94 4-CF₃-phenylOCH₃ CH₃ H  95 2-CH₃-phenyl OCH₃ CH₃ H  96 3-CH₃-phenyl OCH₃ CH₃ H  974-CH₃-phenyl OCH₃ CH₃ H  98 2-NO₂-phenyl OCH₃ CH₃ H  99 3-NO₂-phenylOCH₃ CH₃ H  00 4-NO₂-phenyl OCH₃ CH₃ H 101 2-pyridyl OCH₃ CH₃ H 1023-pyridyl OCH₃ CH₃ H 103 4-pyridyl OCH₃ CH₃ H 104 cyclohexylamino OCH₃CH₃ H 105 cyclopentylamino OCH₃ CH₃ H 106 H Cl CH₃ H 107 CH₃ Cl CH₃ H108 C₂H₅ Cl CH₃ H 109 n-C₃H₇ Cl CH₃ H 110 i-C₃H₇ Cl CH₃ H 111 n-C₄H₉ ClCH₃ H 112 s-C₄H₉ Cl CH₃ H 113 i-C₄H₉ Cl CH₃ H 114 t-C₄H₉ Cl CH₃ H 115CH₂Cl Cl CH₃ H 116 CHCl₂ Cl CH₃ H 117 CCl₃ Cl CH₃ H 118 CH₂F Cl CH₃ H119 CHF₂ Cl CH₃ H 120 CF₃ Cl CH₃ H 121 CH₂CF₃ Cl CH₃ H 122 CH₂OCH₃ ClCH₃ H 123 CH₂OCH₂CH₃ Cl CH₃ H 124 CH₂NH₂ Cl CH₃ H 125 (CH₂)₂COCH₃ Cl CH₃H 126 phenyl Cl CH₃ H 127 2-F-phenyl Cl CH₃ H 128 3-F-phenyl Cl CH₃ H129 4-F-phenyl Cl CH₃ H 130 2-Cl-phenyl Cl CH₃ H 131 3-Cl-phenyl Cl CH₃H 132 4-Cl-phenyl Cl CH₃ H 133 2-OH-phenyl Cl CH₃ H 134 3-OH-phenyl ClCH₃ H 135 4-OH-phenyl Cl CH₃ H 136 2-OCH₃-phenyl Cl CH₃ H 1373-OCH₃-phenyl Cl CH₃ H 138 4-OCH₃-phenyl Cl CH₃ H 139 2-OCF₃-phenyl ClCH₃ H 140 3-OCF₃-phenyl Cl CH₃ H 141 4-OCF₃-phenyl Cl CH₃ H 1422-OCHF₂-phenyl Cl CH₃ H 143 3-OCHF₂-phenyl Cl CH₃ H 144 4-OCHF₂-phenylCl CH₃ H 145 2-CF₃-phenyl Cl CH₃ H 146 3-CF₃-phenyl Cl CH₃ H 1474-CF₃-phenyl Cl CH₃ H 148 2-CH₃-phenyl Cl CH₃ H 149 3-CH₃-phenyl Cl CH₃H 150 4-CH₃-phenyl Cl CH₃ H 151 2-NO₂-phenyl Cl CH₃ H 152 3-NO₂-phenylCl CH₃ H 153 4-NO₂-phenyl Cl CH₃ H 154 2-pyridyl Cl CH₃ H 155 3-pyridylCl CH₃ H 156 4-pyridyl Cl CH₃ H 157 cyclohexylamino Cl CH₃ H 158cyclopentylamino Cl CH₃ H 159 CH₃ CH₃ H H 160 C₂H₅ CH₃ H H 161 n-C₃H₇CH₃ H H 162 i-C₃H₇ CH₃ H H 163 n-C₄H₉ CH₃ H H 164 s-C₄H₉ CH₃ H H 165i-C₄H₉ CH₃ H H 166 t-C₄H₉ CH₃ H H 167 CH₂Cl CH₃ H H 168 CHCl₂ CH₃ H H169 CCl₃ CH₃ H H 170 CH₂F CH₃ H H 171 CHF₂ CH₃ H H 172 CF₃ CH₃ H H 173CH₂CF₃ CH₃ H H 174 CH₂OCH₃ CH₃ H H 175 CH₂OCH₂CH₃ CH₃ H H 176 CH₂NH₂ CH₃H H 177 (CH₂)₂COCH₃ CH₃ H H 178 phenyl CH₃ H H 179 2-F-phenyl CH₃ H H180 3-F-phenyl CH₃ H H 181 4-F-phenyl CH₃ H H 182 2-Cl-phenyl CH₃ H H183 3-Cl-phenyl CH₃ H H 184 4-Cl-phenyl CH₃ H H 185 2-OH-phenyl CH₃ H H186 3-OH-phenyl CH₃ H H 187 4-OH-phenyl CH₃ H H 188 2-OCH₃-phenyl CH₃ HH 189 3-OCH₃-phenyl CH₃ H H 190 4-OCH₃-phenyl CH₃ H H 191 2-OCF₃-phenylCH₃ H H 192 3-OCF₃-phenyl CH₃ H H 193 4-OCF₃-phenyl CH₃ H H 1942-OCHF₂-phenyl CH₃ H H 195 3-OCHF₂-phenyl CH₃ H H 196 4-OCHF₂-phenyl CH₃H H 197 2-CF₃-phenyl CH₃ H H 198 3-CF₃-phenyl CH₃ H H 199 4-CF₃-phenylCH₃ H H 200 2-CH₃-phenyl CH₃ H H 201 3-CH₃-phenyl CH₃ H H 2024-CH₃-phenyl CH₃ H H 203 2-NO₂-phenyl CH₃ H H 204 3-NO₂-phenyl CH₃ H H205 4-NO₂-phenyl CH₃ H H 206 2-pyridyl CH₃ H H 207 3-pyridyl CH₃ H H 2084-pyridyl CH₃ H H 209 cyclohexylamino CH₃ H H 210 cyclopentylamino CH₃ HH 211 H OCH₃ H H 212 CH₃ OCH₃ H H 213 C₂H₅ OCH₃ H H 214 n-C₃H₇ OCH₃ H H215 i-C₃H₇ OCH₃ H H 216 n-C₄H₉ OCH₃ H H 217 s-C₄H₉ OCH₃ H H 218 i-C₄H₉OCH₃ H H 219 t-C₄H₉ OCH₃ H H 220 CH₂Cl OCH₃ H H 221 CHCl₂ OCH₃ H H 222CCl₃ OCH₃ H H 223 CH₂F OCH₃ H H 224 CHF₂ OCH₃ H H 225 CF₃ OCH₃ H H 226CH₂CF₃ OCH₃ H H 227 CH₂OCH₃ OCH₃ H H 228 CH₂OCH₂CH₃ OCH₃ H H 229 CH₂NH₂OCH₃ H H 230 (CH₂)₂COCH₃ OCH₃ H H 231 phenyl OCH₃ H H 232 2-F-phenylOCH₃ H H 233 3-F-phenyl OCH₃ H H 234 4-F-phenyl OCH₃ H H 235 2-Cl-phenylOCH₃ H H 236 3-Cl-phenyl OCH₃ H H 237 4-Cl-phenyl OCH₃ H H 2382-OH-phenyl OCH₃ H H 239 3-OH-phenyl OCH₃ H H 240 4-OH-phenyl OCH₃ H H241 2-OCH₃-phenyl OCH₃ H H 242 3-OCH₃-phenyl OCH₃ H H 243 4-OCH₃-phenylOCH₃ H H 244 2-OCF₃-phenyl OCH₃ H H 245 3-OCF₃-phenyl OCH₃ H H 2464-OCF₃-phenyl OCH₃ H H 247 2-OCHF₂-phenyl OCH₃ H H 248 3-OCHF₂-phenylOCH₃ H H 249 4-OCHF₂-phenyl OCH₃ H H 250 2-CF₃-phenyl OCH₃ H H 2513-CF₃-phenyl OCH₃ H H 252 4-CF₃-phenyl OCH₃ H H 253 2-CH₃-phenyl OCH₃ HH 254 3-CH₃-phenyl OCH₃ H H 255 4-CH₃-phenyl OCH₃ H H 256 2-NO₂-phenylOCH₃ H H 257 3-NO₂-phenyl OCH₃ H H 258 4-NO₂-phenyl OCH₃ H H 2592-pyridyl OCH₃ H H 260 3-pyridyl OCH₃ H H 261 4-pyridyl OCH₃ H H 262cyclohexylamino OCH₃ H H 263 cyclopentylamino OCH₃ H H 264 H Cl H H 265CH₃ Cl H H 266 C₂H₅ Cl H H 267 n-C₃H₇ Cl H H 268 i-C₃H₇ Cl H H 269n-C₄H₉ Cl H H 270 s-C₄H₉ Cl H H 271 i-C₄H₉ Cl H H 272 t-C₄H₉ Cl H H 273CH₂Cl Cl H H 274 CHCl₂ Cl H H 275 CCl₃ Cl H H 276 CH₂F Cl H H 277 CHF₂Cl H H 278 CF₃ Cl H H 279 CH₂CF₃ Cl H H 280 CH₂OCH₃ Cl H H 281CH₂OCH₂CH₃ Cl H H 282 CH₂NH₂ Cl H H 283 (CH₂)₂COCH₃ Cl H H 284 phenyl ClH H 285 2-F-phenyl Cl H H 286 3-F-phenyl Cl H H 287 4-F-phenyl Cl H H288 2-Cl-phenyl Cl H H 289 3-Cl-phenyl Cl H H 290 4-Cl-phenyl Cl H H 2912-OH-phenyl Cl H H 292 3-OH-phenyl Cl H H 293 4-OH-phenyl Cl H H 2942-OCH₃-phenyl Cl H H 295 3-OCH₃-phenyl Cl H H 296 4-OCH₃-phenyl Cl H H297 2-OCF₃-phenyl Cl H H 298 3-OCF₃-phenyl Cl H H 299 4-OCF₃-phenyl Cl HH 300 2-OCHF₂-phenyl Cl H H 301 3-OCHF₂-phenyl Cl H H 302 4-OCHF₂-phenylCl H H 303 2-CF₃-phenyl Cl H H 304 3-CF₃-phenyl Cl H H 305 4-CF₃-phenylCl H H 306 2-CH₃-phenyl Cl H H 307 3-CH₃-phenyl Cl H H 308 4-CH₃-phenylCl H H 309 2-NO₂-phenyl Cl H H 310 3-NO₂-phenyl Cl H H 311 4-NO₂-phenylCl H H 312 2-pyridyl Cl H H 313 3-pyridyl Cl H H 314 4-pyridyl Cl H H315 cyclohexylamino Cl H H 316 cyclopentylamino Cl H H 317 CH₃ CH₃ CH₃CH₃ 318 C₂H₅ CH₃ CH₃ CH₃ 319 n-C₃H₇ CH₃ CH₃ CH₃ 320 i-C₃H₇ CH₃ CH₃ CH₃321 n-C₄H₉ CH₃ CH₃ CH₃ 322 s-C₄H₉ CH₃ CH₃ CH₃ 323 i-C₄H₉ CH₃ CH₃ CH₃ 324t-C₄H₉ CH₃ CH₃ CH₃ 325 CH₂Cl CH₃ CH₃ CH₃ 326 CHCl₂ CH₃ CH₃ CH₃ 327 CCl₃CH₃ CH₃ CH₃ 328 CH₂F CH₃ CH₃ CH₃ 329 CHF₂ CH₃ CH₃ CH₃ 330 CF₃ CH₃ CH₃CH₃ 331 CH₂CF₃ CH₃ CH₃ CH₃ 332 CH₂OCH₃ CH₃ CH₃ CH₃ 333 CH₂OCH₂CH₃ CH₃CH₃ CH₃ 334 CH₂NH₂ CH₃ CH₃ CH₃ 335 (CH₂)₂COCH₃ CH₃ CH₃ CH₃ 336 phenylCH₃ CH₃ CH₃ 337 2-F-phenyl CH₃ CH₃ CH₃ 338 3-F-phenyl CH₃ CH₃ CH₃ 3394-F-phenyl CH₃ CH₃ CH₃ 340 2-Cl-phenyl CH₃ CH₃ CH₃ 341 3-Cl-phenyl CH₃CH₃ CH₃ 342 4-Cl-phenyl CH₃ CH₃ CH₃ 343 2-OH-phenyl CH₃ CH₃ CH₃ 3443-OH-phenyl CH₃ CH₃ CH₃ 345 4-OH-phenyl CH₃ CH₃ CH₃ 346 2-OCH₃-phenylCH₃ CH₃ CH₃ 347 3-OCH₃-phenyl CH₃ CH₃ CH₃ 348 4-OCH₃-phenyl CH₃ CH₃ CH₃349 2-OCF₃-phenyl CH₃ CH₃ CH₃ 350 3-OCF₃-phenyl CH₃ CH₃ CH₃ 3514-OCF₃-phenyl CH₃ CH₃ CH₃ 352 2-OCHF₂-phenyl CH₃ CH₃ CH₃ 3533-OCHF₂-phenyl CH₃ CH₃ CH₃ 354 4-OCHF₂-phenyl CH₃ CH₃ CH₃ 3552-CF₃-phenyl CH₃ CH₃ CH₃ 356 3-CF₃-phenyl CH₃ CH₃ CH₃ 357 4-CF₃-phenylCH₃ CH₃ CH₃ 358 2-CH₃-phenyl CH₃ CH₃ CH₃ 359 3-CH₃-phenyl CH₃ CH₃ CH₃360 4-CH₃-phenyl CH₃ CH₃ CH₃ 361 2-NO₂-phenyl CH₃ CH₃ CH₃ 3623-NO₂-phenyl CH₃ CH₃ CH₃ 363 4-NO₂-phenyl CH₃ CH₃ CH₃ 364 2-pyridyl CH₃CH₃ CH₃ 365 3-pyridyl CH₃ CH₃ CH₃ 366 4-pyridyl CH₃ CH₃ CH₃ 367cyclohexylamino CH₃ CH₃ CH₃ 368 cyclopentylamino CH₃ CH₃ CH₃ 369 H OCH₃CH₃ CH₃ 370 CH₃ OCH₃ CH₃ CH₃ 371 C₂H₅ OCH₃ CH₃ CH₃ 372 n-C₃H₇ OCH₃ CH₃CH₃ 373 i-C₃H₇ OCH₃ CH₃ CH₃ 374 n-C₄H₉ OCH₃ CH₃ CH₃ 375 s-C₄H₉ OCH₃ CH₃CH₃ 376 i-C₄H₉ OCH₃ CH₃ CH₃ 377 t-C₄H₉ OCH₃ CH₃ CH₃ 378 CH₂Cl OCH₃ CH₃CH₃ 379 CHCl₂ OCH₃ CH₃ CH₃ 380 CCl₃ OCH₃ CH₃ CH₃ 381 CH₂F OCH₃ CH₃ CH₃382 CHF₂ OCH₃ CH₃ CH₃ 383 CF₃ OCH₃ CH₃ CH₃ 384 CH₂CF₃ OCH₃ CH₃ CH₃ 385CH₂OCH₃ OCH₃ CH₃ CH₃ 386 CH₂OCH₂CH₃ OCH₃ CH₃ CH₃ 387 CH₂NH₂ OCH₃ CH₃ CH₃388 (CH₂)₂COCH₃ OCH₃ CH₃ CH₃ 389 phenyl OCH₃ CH₃ CH₃ 390 2-F-phenyl OCH₃CH₃ CH₃ 391 3-F-phenyl OCH₃ CH₃ CH₃ 392 4-F-phenyl OCH₃ CH₃ CH₃ 3932-Cl-phenyl OCH₃ CH₃ CH₃ 394 3-Cl-phenyl OCH₃ CH₃ CH₃ 395 4-Cl-phenylOCH₃ CH₃ CH₃ 396 2-OH-phenyl OCH₃ CH₃ CH₃ 397 3-OH-phenyl OCH₃ CH₃ CH₃398 4-OH-phenyl OCH₃ CH₃ CH₃ 399 2-OCH₃-phenyl OCH₃ CH₃ CH₃ 4003-OCH₃-phenyl OCH₃ CH₃ CH₃ 401 4-OCH₃-phenyl OCH₃ CH₃ CH₃ 4022-OCF₃-phenyl OCH₃ CH₃ CH₃ 403 3-OCF₃-phenyl OCH₃ CH₃ CH₃ 4044-OCF₃-phenyl OCH₃ CH₃ CH₃ 405 2-OCHF₂-phenyl OCH₃ CH₃ CH₃ 4063-OCHF₂-phenyl OCH₃ CH₃ CH₃ 407 4-OCHF₂-phenyl OCH₃ CH₃ CH₃ 4082-CF₃-phenyl OCH₃ CH₃ CH₃ 409 3-CF₃-phenyl OCH₃ CH₃ CH₃ 410 4-CF₃-phenylOCH₃ CH₃ CH₃ 411 2-CH₃-phenyl OCH₃ CH₃ CH₃ 412 3-CH₃-phenyl OCH₃ CH₃ CH₃413 4-CH₃-phenyl OCH₃ CH₃ CH₃ 414 2-NO₂-phenyl OCH₃ CH₃ CH₃ 4153-NO₂-phenyl OCH₃ CH₃ CH₃ 416 4-NO₂-phenyl OCH₃ CH₃ CH₃ 417 2-pyridylOCH₃ CH₃ CH₃ 418 3-pyridyl OCH₃ CH₃ CH₃ 419 4-pyridyl OCH₃ CH₃ CH₃ 420cyclohexylamino OCH₃ CH₃ CH₃ 421 cyclopentylamino OCH₃ CH₃ CH₃ 422 H ClCH₃ CH₃ 423 CH₃ Cl CH₃ CH₃ 424 C₂H₅ Cl CH₃ CH₃ 445 n-C₃H₇ Cl CH₃ CH₃ 426i-C₃H₇ Cl CH₃ CH₃ 427 n-C₄H₉ Cl CH₃ CH₃ 428 s-C₄H₉ Cl CH₃ CH₃ 429 i-C₄H₉Cl CH₃ CH₃ 430 t-C₄H₉ Cl CH₃ CH₃ 431 CH₂Cl Cl CH₃ CH₃ 432 CHCl₂ Cl CH₃CH₃ 433 CCl₃ Cl CH₃ CH₃ 434 CH₂F Cl CH₃ CH₃ 435 CHF₂ Cl CH₃ CH₃ 436 CF₃Cl CH₃ CH₃ 437 CH₂CF₃ Cl CH₃ CH₃ 438 CH₂OCH₃ Cl CH₃ CH₃ 439 CH₂OCH₂CH₃Cl CH₃ CH₃ 440 CH₂NH₂ Cl CH₃ CH₃ 441 (CH₂)₂COCH₃ Cl CH₃ CH₃ 442 phenylCl CH₃ CH₃ 443 2-F-phenyl Cl CH₃ CH₃ 444 3-F-phenyl Cl CH₃ CH₃ 4454-F-phenyl Cl CH₃ CH₃ 446 2-Cl-phenyl Cl CH₃ CH₃ 447 3-Cl-phenyl Cl CH₃CH₃ 448 4-Cl-phenyl Cl CH₃ CH₃ 449 2-OH-phenyl Cl CH₃ CH₃ 4503-OH-phenyl Cl CH₃ CH₃ 451 4-OH-phenyl Cl CH₃ CH₃ 452 2-OCH₃-phenyl ClCH₃ CH₃ 453 3-OCH₃-phenyl Cl CH₃ CH₃ 454 4-OCH₃-phenyl Cl CH₃ CH₃ 4552-OCF₃-phenyl Cl CH₃ CH₃ 456 3-OCF₃-phenyl Cl CH₃ CH₃ 457 4-OCF₃-phenylCl CH₃ CH₃ 458 2-OCHF₂-phenyl Cl CH₃ CH₃ 459 3-OCHF₂-phenyl Cl CH₃ CH₃460 4-OCHF₂-phenyl Cl CH₃ CH₃ 461 2-CF₃-phenyl Cl CH₃ CH₃ 4623-CF₃-phenyl Cl CH₃ CH₃ 463 4-CF₃-phenyl Cl CH₃ CH₃ 464 2-CH₃-phenyl ClCH₃ CH₃ 465 3-CH₃-phenyl Cl CH₃ CH₃ 466 4-CH₃-phenyl Cl CH₃ CH₃ 4672-NO₂-phenyl Cl CH₃ CH₃ 468 3-NO₂-phenyl Cl CH₃ CH₃ 469 4-NO₂-phenyl ClCH₃ CH₃ 470 2-pyridyl Cl CH₃ CH₃ 471 3-pyridyl Cl CH₃ CH₃ 472 4-pyridylCl CH₃ CH₃ 473 cyclohexylamino Cl CH₃ CH₃ 474 cyclopentylamino Cl CH₃CH₃ 475 CH₃ CH₃ H CH₃ 476 C₂H₅ CH₃ H CH₃ 477 n-C₃H₇ CH₃ H CH₃ 478 i-C₃H₇CH₃ H CH₃ 479 n-C₄H₉ CH₃ H CH₃ 480 s-C₄H₉ CH₃ H CH₃ 481 i-C₄H₉ CH₃ H CH₃482 t-C₄H₉ CH₃ H CH₃ 483 CH₂Cl CH₃ H CH₃ 484 CHCl₂ CH₃ H CH₃ 485 CCl₃CH₃ H CH₃ 486 CH₂F CH₃ H CH₃ 487 CHF₂ CH₃ H CH₃ 488 CF₃ CH₃ H CH₃ 489CH₂CF₃ CH₃ H CH₃ 490 CH₂OCH₃ CH₃ H CH₃ 491 CH₂OCH₂CH₃ CH₃ H CH₃ 492CH₂NH₂ CH₃ H CH₃ 493 (CH₂)₂COCH₃ CH₃ H CH₃ 494 phenyl CH₃ H CH₃ 4952-F-phenyl CH₃ H CH₃ 496 3-F-phenyl CH₃ H CH₃ 497 4-F-phenyl CH₃ H CH₃498 2-Cl-phenyl CH₃ H CH₃ 499 3-Cl-phenyl CH₃ H CH₃ 500 4-Cl-phenyl CH₃H CH₃ 501 2-OH-phenyl CH₃ H CH₃ 502 3-OH-phenyl CH₃ H CH₃ 5034-OH-phenyl CH₃ H CH₃ 504 2-OCH₃-phenyl CH₃ H CH₃ 505 3-OCH₃-phenyl CH₃H CH₃ 506 4-OCH₃-phenyl CH₃ H CH₃ 507 2-OCF₃-phenyl CH₃ H CH₃ 5083-OCF₃-phenyl CH₃ H CH₃ 509 4-OCF₃-phenyl CH₃ H CH₃ 510 2-OCHF₂-phenylCH₃ H CH₃ 511 3-OCHF₂-phenyl CH₃ H CH₃ 512 4-OCHF₂-phenyl CH₃ H CH₃ 5132-CF₃-phenyl CH₃ H CH₃ 514 3-CF₃-phenyl CH₃ H CH₃ 515 4-CF₃-phenyl CH₃ HCH₃ 516 2-CH₃-phenyl CH₃ H CH₃ 517 3-CH₃-phenyl CH₃ H CH₃ 5184-CH₃-phenyl CH₃ H CH₃ 519 2-NO₂-phenyl CH₃ H CH₃ 520 3-NO₂-phenyl CH₃ HCH₃ 521 4-NO₂-phenyl CH₃ H CH₃ 522 2-pyridyl CH₃ H CH₃ 523 3-pyridyl CH₃H CH₃ 524 4-pyridyl CH₃ H CH₃ 525 cyclohexylamino CH₃ H CH₃ 526cyclopentylamino CH₃ H CH₃ 527 H OCH₃ H CH₃ 528 CH₃ OCH₃ H CH₃ 529 C₂H₅OCH₃ H CH₃ 530 n-C₃H₇ OCH₃ H CH₃ 531 i-C₃H₇ OCH₃ H CH₃ 532 n-C₄H₉ OCH₃ HCH₃ 533 s-C₄H₉ OCH₃ H CH₃ 534 i-C₄H₉ OCH₃ H CH₃ 535 t-C₄H₉ OCH₃ H CH₃536 CH₂Cl OCH₃ H CH₃ 537 CHCl₂ OCH₃ H CH₃ 538 CCl₃ OCH₃ H CH₃ 539 CH₂FOCH₃ H CH₃ 540 CHF₂ OCH₃ H CH₃ 541 CF₃ OCH₃ H CH₃ 542 CH₂CF₃ OCH₃ H CH₃543 CH₂OCH₃ OCH₃ H CH₃ 544 CH₂OCH₂CH₃ OCH₃ H CH₃ 545 CH₂NH₂ OCH₃ H CH₃546 (CH₂)₂COCH₃ OCH₃ H CH₃ 547 phenyl OCH₃ H CH₃ 548 2-F-phenyl OCH₃ HCH₃ 549 3-F-phenyl OCH₃ H CH₃ 550 4-F-phenyl OCH₃ H CH₃ 551 2-Cl-phenylOCH₃ H CH₃ 552 3-Cl-phenyl OCH₃ H CH₃ 553 4-Cl-phenyl OCH₃ H CH₃ 5542-OH-phenyl OCH₃ H CH₃ 555 3-OH-phenyl OCH₃ H CH₃ 556 4-OH-phenyl OCH₃ HCH₃ 557 2-OCH₃-phenyl OCH₃ H CH₃ 558 3-OCH₃-phenyl OCH₃ H CH₃ 5594-OCH₃-phenyl OCH₃ H CH₃ 560 2-OCF₃-phenyl OCH₃ H CH₃ 561 3-OCF₃-phenylOCH₃ H CH₃ 562 4-OCF₃-phenyl OCH₃ H CH₃ 563 2-OCHF₂-phenyl OCH₃ H CH₃564 3-OCHF₂-phenyl OCH₃ H CH₃ 565 4-OCHF₂-phenyl OCH₃ H CH₃ 5662-CF₃-phenyl OCH₃ H CH₃ 567 3-CF₃-phenyl OCH₃ H CH₃ 568 4-CF₃-phenylOCH₃ H CH₃ 569 2-CH₃-phenyl OCH₃ H CH₃ 570 3-CH₃-phenyl OCH₃ H CH₃ 5714-CH₃-phenyl OCH₃ H CH₃ 572 2-NO₂-phenyl OCH₃ H CH₃ 573 3-NO₂-phenylOCH₃ H CH₃ 574 4-NO₂-phenyl OCH₃ H CH₃ 575 2-pyridyl OCH₃ H CH₃ 5763-pyridyl OCH₃ H CH₃ 577 4-pyridyl OCH₃ H CH₃ 578 cyclohexylamino OCH₃ HCH₃ 579 cyclopentylamino OCH₃ H CH₃ 580 H Cl H CH₃ 581 CH₃ Cl H CH₃ 582C₂H₅ Cl H CH₃ 583 n-C₃H₇ Cl H CH₃ 584 i-C₃H₇ Cl H CH₃ 585 n-C₄H₉ Cl HCH₃ 586 s-C₄H₉ Cl H CH₃ 587 i-C₄H₉ Cl H CH₃ 588 t-C₄H₉ Cl H CH₃ 589CH₂Cl Cl H CH₃ 590 CHCl₂ Cl H CH₃ 591 CCl₃ Cl H CH₃ 592 CH₂F Cl H CH₃593 CHF₂ Cl H CH₃ 594 CF₃ Cl H CH₃ 595 CH₂CF₃ Cl H CH₃ 596 CH₂OCH₃ Cl HCH₃ 597 CH₂OCH₂CH₃ Cl H CH₃ 598 CH₂NH₂ Cl H CH₃ 599 (CH₂)₂COCH₃ Cl H CH₃600 phenyl Cl H CH₃ 701 2-F-phenyl Cl H CH₃ 702 3-F-phenyl Cl H CH₃ 7034-F-phenyl Cl H CH₃ 704 2-Cl-phenyl Cl H CH₃ 705 3-Cl-phenyl Cl H CH₃706 4-Cl-phenyl Cl H CH₃ 707 2-OH-phenyl Cl H CH₃ 708 3-OH-phenyl Cl HCH₃ 709 4-OH-phenyl Cl H CH₃ 710 2-OCH₃-phenyl Cl H CH₃ 7113-OCH₃-phenyl Cl H CH₃ 712 4-OCH₃-phenyl Cl H CH₃ 713 2-OCF₃-phenyl Cl HCH₃ 714 3-OCF₃-phenyl Cl H CH₃ 715 4-OCF₃-phenyl Cl H CH₃ 7162-OCHF₂-phenyl Cl H CH₃ 717 3-OCHF₂-phenyl Cl H CH₃ 718 4-OCHF₂-phenylCl H CH₃ 719 2-CF₃-phenyl Cl H CH₃ 720 3-CF₃-phenyl Cl H CH₃ 7214-CF₃-phenyl Cl H CH₃ 722 2-CH₃-phenyl Cl H CH₃ 723 3-CH₃-phenyl Cl HCH₃ 724 4-CH₃-phenyl Cl H CH₃ 725 2-NO₂-phenyl Cl H CH₃ 726 3-NO₂-phenylCl H CH₃ 727 4-NO₂-phenyl Cl H CH₃ 728 2-pyridyl Cl H CH₃ 729 3-pyridylCl H CH₃ 730 4-pyridyl Cl H CH₃ 731 cyclohexylamino Cl H CH₃ 732cyclopentylamino Cl H CH₃ 733 CH₃ CH₃ CH₃ C₂H₅ 734 C₂H₅ CH₃ CH₃ C₂H₅ 735n-C₃H₇ CH₃ CH₃ C₂H₅ 736 i-C₃H₇ CH₃ CH₃ C₂H₅ 737 n-C₄H₉ CH₃ CH₃ C₂H₅ 738s-C₄H₉ CH₃ CH₃ C₂H₅ 739 i-C₄H₉ CH₃ CH₃ C₂H₅ 740 t-C₄H₉ CH₃ CH₃ C₂H₅ 741CH₂Cl CH₃ CH₃ C₂H₅ 742 CHCl₂ CH₃ CH₃ C₂H₅ 743 CCl₃ CH₃ CH₃ C₂H₅ 744 CH₂FCH₃ CH₃ C₂H₅ 745 CHF₂ CH₃ CH₃ C₂H₅ 746 CF₃ CH₃ CH₃ C₂H₅ 747 CH₂CF₃ CH₃CH₃ C₂H₅ 748 CH₂OCH₃ CH₃ CH₃ C₂H₅ 749 CH₂OCH₂CH₃ CH₃ CH₃ C₂H₅ 750 CH₂NH₂CH₃ CH₃ C₂H₅ 751 (CH₂)₂COCH₃ CH₃ CH₃ C₂H₅ 752 phenyl CH₃ CH₃ C₂H₅ 7532-F-phenyl CH₃ CH₃ C₂H₅ 754 3-F-phenyl CH₃ CH₃ C₂H₅ 755 4-F-phenyl CH₃CH₃ C₂H₅ 756 2-Cl-phenyl CH₃ CH₃ C₂H₅ 757 3-Cl-phenyl CH₃ CH₃ C₂H₅ 7584-Cl-phenyl CH₃ CH₃ C₂H₅ 759 2-OH-phenyl CH₃ CH₃ C₂H₅ 760 3-OH-phenylCH₃ CH₃ C₂H₅ 761 4-OH-phenyl CH₃ CH₃ C₂H₅ 762 2-OCH₃-phenyl CH₃ CH₃ C₂H₅763 3-OCH₃-phenyl CH₃ CH₃ C₂H₅ 764 4-OCH₃-phenyl CH₃ CH₃ C₂H₅ 7652-OCF₃-phenyl CH₃ CH₃ C₂H₅ 766 3-OCF₃-phenyl CH₃ CH₃ C₂H₅ 7674-OCF₃-phenyl CH₃ CH₃ C₂H₅ 768 2-OCHF₂-phenyl CH₃ CH₃ C₂H₅ 7693-OCHF₂-phenyl CH₃ CH₃ C₂H₅ 770 4-OCHF₂-phenyl CH₃ CH₃ C₂H₅ 7712-CF₃-phenyl CH₃ CH₃ C₂H₅ 772 3-CF₃-phenyl CH₃ CH₃ C₂H₅ 773 4-CF₃-phenylCH₃ CH₃ C₂H₅ 774 2-CH₃-phenyl CH₃ CH₃ C₂H₅ 775 3-CH₃-phenyl CH₃ CH₃ C₂H₅776 4-CH₃-phenyl CH₃ CH₃ C₂H₅ 777 2-NO₂-phenyl CH₃ CH₃ C₂H₅ 7783-NO₂-phenyl CH₃ CH₃ C₂H₅ 779 4-NO₂-phenyl CH₃ CH₃ C₂H₅ 780 2-pyridylCH₃ CH₃ C₂H₅ 781 3-pyridyl CH₃ CH₃ C₂H₅ 782 4-pyridyl CH₃ CH₃ C₂H₅ 783cyclohexylamino CH₃ CH₃ C₂H₅ 784 cyclopentylamino CH₃ CH₃ C₂H₅ 785 HOCH₃ CH₃ C₂H₅ 786 CH₃ OCH₃ CH₃ C₂H₅ 787 C₂H₅ OCH₃ CH₃ C₂H₅ 788 n-C₃H₇OCH₃ CH₃ C₂H₅ 789 i-C₃H₇ OCH₃ CH₃ C₂H₅ 790 n-C₄H₉ OCH₃ CH₃ C₂H₅ 791s-C₄H₉ OCH₃ CH₃ C₂H₅ 792 i-C₄H₉ OCH₃ CH₃ C₂H₅ 793 t-C₄H₉ OCH₃ CH₃ C₂H₅794 CH₂Cl OCH₃ CH₃ C₂H₅ 795 CHCl₂ OCH₃ CH₃ C₂H₅ 796 CCl₃ OCH₃ CH₃ C₂H₅797 CH₂F OCH₃ CH₃ C₂H₅ 798 CHF₂ OCH₃ CH₃ C₂H₅ 799 CF₃ OCH₃ CH₃ C₂H₅ 800CH₂CF₃ OCH₃ CH₃ C₂H₅ 801 CH₂OCH₃ OCH₃ CH₃ C₂H₅ 802 CH₂OCH₂CH₃ OCH₃ CH₃C₂H₅ 803 CH₂NH₂ OCH₃ CH₃ C₂H₅ 804 (CH₂)₂COCH₃ OCH₃ CH₃ C₂H₅ 805 phenylOCH₃ CH₃ C₂H₅ 806 2-F-phenyl OCH₃ CH₃ C₂H₅ 807 3-F-phenyl OCH₃ CH₃ C₂H₅808 4-F-phenyl OCH₃ CH₃ C₂H₅ 809 2-Cl-phenyl OCH₃ CH₃ C₂H₅ 8103-Cl-phenyl OCH₃ CH₃ C₂H₅ 811 4-Cl-phenyl OCH₃ CH₃ C₂H₅ 812 2-OH-phenylOCH₃ CH₃ C₂H₅ 813 3-OH-phenyl OCH₃ CH₃ C₂H₅ 814 4-OH-phenyl OCH₃ CH₃C₂H₅ 815 2-OCH₃-phenyl OCH₃ CH₃ C₂H₅ 816 3-OCH₃-phenyl OCH₃ CH₃ C₂H₅ 8174-OCH₃-phenyl OCH₃ CH₃ C₂H₅ 818 2-OCF₃-phenyl OCH₃ CH₃ C₂H₅ 8193-OCF₃-phenyl OCH₃ CH₃ C₂H₅ 820 4-OCF₃-phenyl OCH₃ CH₃ C₂H₅ 8212-OCHF₂-phenyl OCH₃ CH₃ C₂H₅ 822 3-OCHF₂-phenyl OCH₃ CH₃ C₂H₅ 8234-OCHF₂-phenyl OCH₃ CH₃ C₂H₅ 824 2-CF₃-phenyl OCH₃ CH₃ C₂H₅ 8253-CF₃-phenyl OCH₃ CH₃ C₂H₅ 826 4-CF₃-phenyl OCH₃ CH₃ C₂H₅ 8272-CH₃-phenyl OCH₃ CH₃ C₂H₅ 828 3-CH₃-phenyl OCH₃ CH₃ C₂H₅ 8294-CH₃-phenyl OCH₃ CH₃ C₂H₅ 830 2-NO₂-phenyl OCH₃ CH₃ C₂H₅ 8313-NO₂-phenyl OCH₃ CH₃ C₂H₅ 832 4-NO₂-phenyl OCH₃ CH₃ C₂H₅ 833 2-pyridylOCH₃ CH₃ C₂H₅ 834 3-pyridyl OCH₃ CH₃ C₂H₅ 835 4-pyridyl OCH₃ CH₃ C₂H₅836 cyclohexylamino OCH₃ CH₃ C₂H₅ 837 cyclopentylamino OCH₃ CH₃ C₂H₅ 838H Cl CH₃ C₂H₅ 839 CH₃ Cl CH₃ C₂H₅ 840 C₂H₅ Cl CH₃ C₂H₅ 841 n-C₃H₇ Cl CH₃C₂H₅ 842 i-C₃H₇ Cl CH₃ C₂H₅ 843 n-C₄H₉ Cl CH₃ C₂H₅ 844 s-C₄H₉ Cl CH₃C₂H₅ 845 i-C₄H₉ Cl CH₃ C₂H₅ 846 t-C₄H₉ Cl CH₃ C₂H₅ 847 CH₂Cl Cl CH₃ C₂H₅848 CHCl₂ Cl CH₃ C₂H₅ 849 CCl₃ Cl CH₃ C₂H₅ 850 CH₂F Cl CH₃ C₂H₅ 851 CHF₂Cl CH₃ C₂H₅ 852 CF₃ Cl CH₃ C₂H₅ 853 CH₂CF₃ Cl CH₃ C₂H₅ 854 CH₂OCH₃ ClCH₃ C₂H₅ 855 CH₂OCH₂CH₃ Cl CH₃ C₂H₅ 856 CH₂NH₂ Cl CH₃ C₂H₅ 857(CH₂)₂COCH₃ Cl CH₃ C₂H₅ 858 phenyl Cl CH₃ C₂H₅ 859 2-F-phenyl Cl CH₃C₂H₅ 860 3-F-phenyl Cl CH₃ C₂H₅ 861 4-F-phenyl Cl CH₃ C₂H₅ 8622-Cl-phenyl Cl CH₃ C₂H₅ 863 3-Cl-phenyl Cl CH₃ C₂H₅ 864 4-Cl-phenyl ClCH₃ C₂H₅ 865 2-OH-phenyl Cl CH₃ C₂H₅ 866 3-OH-phenyl Cl CH₃ C₂H₅ 8674-OH-phenyl Cl CH₃ C₂H₅ 868 2-OCH₃-phenyl Cl CH₃ C₂H₅ 869 3-OCH₃-phenylCl CH₃ C₂H₅ 870 4-OCH₃-phenyl Cl CH₃ C₂H₅ 871 2-OCF₃-phenyl Cl CH₃ C₂H₅872 3-OCF₃-phenyl Cl CH₃ C₂H₅ 873 4-OCF₃-phenyl Cl CH₃ C₂H₅ 8742-OCHF₂-phenyl Cl CH₃ C₂H₅ 875 3-OCHF₂-phenyl Cl CH₃ C₂H₅ 8764-OCHF₂-phenyl Cl CH₃ C₂H₅ 877 2-CF₃-phenyl Cl CH₃ C₂H₅ 878 3-CF₃-phenylCl CH₃ C₂H₅ 879 4-CF₃-phenyl Cl CH₃ C₂H₅ 880 2-CH₃-phenyl Cl CH₃ C₂H₅881 3-CH₃-phenyl Cl CH₃ C₂H₅ 882 4-CH₃-phenyl Cl CH₃ C₂H₅ 8832-NO₂-phenyl Cl CH₃ C₂H₅ 884 3-NO₂-phenyl Cl CH₃ C₂H₅ 885 4-NO₂-phenylCl CH₃ C₂H₅ 886 2-pyridyl Cl CH₃ C₂H₅ 887 3-pyridyl Cl CH₃ C₂H₅ 8884-pyridyl Cl CH₃ C₂H₅ 889 cyclohexylamino Cl CH₃ C₂H₅ 890cyclopentylamino Cl CH₃ C₂H₅ 891 CH₃ CH₃ H C₂H₅ 892 C₂H₅ CH₃ H C₂H₅ 893n-C₃H₇ CH₃ H C₂H₅ 894 i-C₃H₇ CH₃ H C₂H₅ 895 n-C₄H₉ CH₃ H C₂H₅ 896 s-C₄H₉CH₃ H C₂H₅ 897 i-C₄H₉ CH₃ H C₂H₅ 898 t-C₄H₉ CH₃ H C₂H₅ 899 CH₂Cl CH₃ HC₂H₅ 900 CHCl₂ CH₃ H C₂H₅ 901 CCl₃ CH₃ H C₂H₅ 902 CH₂F CH₃ H C₂H₅ 903CHF₂ CH₃ H C₂H₅ 904 CF₃ CH₃ H C₂H₅ 905 CH₂CF₃ CH₃ H C₂H₅ 906 CH₂OCH₃ CH₃H C₂H₅ 907 CH₂OCH₂CH₃ CH₃ H C₂H₅ 908 CH₂NH₂ CH₃ H C₂H₅ 909 (CH₂)₂COCH₃CH₃ H C₂H₅ 910 phenyl CH₃ H C₂H₅ 911 2-F-phenyl CH₃ H C₂H₅ 9123-F-phenyl CH₃ H C₂H₅ 913 4-F-phenyl CH₃ H C₂H₅ 914 2-Cl-phenyl CH₃ HC₂H₅ 915 3-Cl-phenyl CH₃ H C₂H₅ 916 4-Cl-phenyl CH₃ H C₂H₅ 9172-OH-phenyl CH₃ H C₂H₅ 918 3-OH-phenyl CH₃ H C₂H₅ 919 4-OH-phenyl CH₃ HC₂H₅ 920 2-OCH₃-phenyl CH₃ H C₂H₅ 921 3-OCH₃-phenyl CH₃ H C₂H₅ 9224-OCH₃-phenyl CH₃ H C₂H₅ 923 2-OCF₃-phenyl CH₃ H C₂H₅ 924 3-OCF₃-phenylCH₃ H C₂H₅ 925 4-OCF₃-phenyl CH₃ H C₂H₅ 926 2-OCHF₂-phenyl CH₃ H C₂H₅927 3-OCHF₂-phenyl CH₃ H C₂H₅ 928 4-OCHF₂-phenyl CH₃ H C₂H₅ 9292-CF₃-phenyl CH₃ H C₂H₅ 930 3-CF₃-phenyl CH₃ H C₂H₅ 931 4-CF₃-phenyl CH₃H C₂H₅ 932 2-CH₃-phenyl CH₃ H C₂H₅ 933 3-CH₃-phenyl CH₃ H C₂H₅ 9344-CH₃-phenyl CH₃ H C₂H₅ 935 2-NO₂-phenyl CH₃ H C₂H₅ 936 3-NO₂-phenyl CH₃H C₂H₅ 937 4-NO₂-phenyl CH₃ H C₂H₅ 938 2-pyridyl CH₃ H C₂H₅ 9393-pyridyl CH₃ H C₂H₅ 940 4-pyridyl CH₃ H C₂H₅ 941 cyclohexylamino CH₃ HC₂H₅ 942 cyclopentylamino CH₃ H C₂H₅ 943 H OCH₃ H C₂H₅ 944 CH₃ OCH₃ HC₂H₅ 945 C₂H₅ OCH₃ H C₂H₅ 946 n-C₃H₇ OCH₃ H C₂H₅ 947 i-C₃H₇ OCH₃ H C₂H₅948 n-C₄H₉ OCH₃ H C₂H₅ 949 s-C₄H₉ OCH₃ H C₂H₅ 950 i-C₄H₉ OCH₃ H C₂H₅ 951t-C₄H₉ OCH₃ H C₂H₅ 952 CH₂Cl OCH₃ H C₂H₅ 953 CHCl₂ OCH₃ H C₂H₅ 954 CCl₃OCH₃ H C₂H₅ 955 CH₂F OCH₃ H C₂H₅ 956 CHF₂ OCH₃ H C₂H₅ 957 CF₃ OCH₃ HC₂H₅ 958 CH₂CF₃ OCH₃ H C₂H₅ 959 CH₂OCH₃ OCH₃ H C₂H₅ 960 CH₂OCH₂CH₃ OCH₃H C₂H₅ 961 CH₂NH₂ OCH₃ H C₂H₅ 962 (CH₂)₂COCH₃ OCH₃ H C₂H₅ 963 phenylOCH₃ H C₂H₅ 964 2-F-phenyl OCH₃ H C₂H₅ 965 3-F-phenyl OCH₃ H C₂H₅ 9664-F-phenyl OCH₃ H C₂H₅ 967 2-Cl-phenyl OCH₃ H C₂H₅ 968 3-Cl-phenyl OCH₃H C₂H₅ 969 4-Cl-phenyl OCH₃ H C₂H₅ 970 2-OH-phenyl OCH₃ H C₂H₅ 9713-OH-phenyl OCH₃ H C₂H₅ 972 4-OH-phenyl OCH₃ H C₂H₅ 973 2-OCH₃-phenylOCH₃ H C₂H₅ 974 3-OCH₃-phenyl OCH₃ H C₂H₅ 975 4-OCH₃-phenyl OCH₃ H C₂H₅976 2-OCF₃-phenyl OCH₃ H C₂H₅ 977 3-OCF₃-phenyl OCH₃ H C₂H₅ 9784-OCF₃-phenyl OCH₃ H C₂H₅ 979 2-OCHF₂-phenyl OCH₃ H C₂H₅ 9803-OCHF₂-phenyl OCH₃ H C₂H₅ 981 4-OCHF₂-phenyl OCH₃ H C₂H₅ 9822-CF₃-phenyl OCH₃ H C₂H₅ 983 3-CF₃-phenyl OCH₃ H C₂H₅ 984 4-CF₃-phenylOCH₃ H C₂H₅ 985 2-CH₃-phenyl OCH₃ H C₂H₅ 986 3-CH₃-phenyl OCH₃ H C₂H₅987 4-CH₃-phenyl OCH₃ H C₂H₅ 988 2-NO₂-phenyl OCH₃ H C₂H₅ 9893-NO₂-phenyl OCH₃ H C₂H₅ 990 4-NO₂-phenyl OCH₃ H C₂H₅ 991 2-pyridyl OCH₃H C₂H₅ 992 3-pyridyl OCH₃ H C₂H₅ 993 4-pyridyl OCH₃ H C₂H₅ 994cyclohexylamino OCH₃ H C₂H₅ 995 cyclopentylamino OCH₃ H C₂H₅ 996 H Cl HC₂H₅ 997 CH₃ Cl H C₂H₅ 998 C₂H₅ Cl H C₂H₅ 999 n-C₃H₇ Cl H C₂H₅ 999i-C₃H₇ Cl H C₂H₅ 1000  n-C₄H₉ Cl H C₂H₅ 1001  s-C₄H₉ Cl H C₂H₅ 1002 i-C₄H₉ Cl H C₂H₅ 1003  t-C₄H₉ Cl H C₂H₅ 1004  CH₂Cl Cl H C₂H₅ 1005 CHCl₂ Cl H C₂H₅ 1006  CCl₃ Cl H C₂H₅ 1007  CH₂F Cl H C₂H₅ 1008  CHF₂ ClH C₂H₅ 1009  CF₃ Cl H C₂H₅ 1010  CH₂CF₃ Cl H C₂H₅ 1011  CH₂OCH₃ Cl HC₂H₅ 1012  CH₂OCH₂CH₃ Cl H C₂H₅ 1013  CH₂NH₂ Cl H C₂H₅ 1014  (CH₂)₂COCH₃Cl H C₂H₅ 1015  phenyl Cl H C₂H₅ 1016  2-F-phenyl Cl H C₂H₅ 1017 3-F-phenyl Cl H C₂H₅ 1018  4-F-phenyl Cl H C₂H₅ 1019  2-Cl-phenyl Cl HC₂H₅ 1020  3-Cl-phenyl Cl H C₂H₅ 1021  4-Cl-phenyl Cl H C₂H₅ 1022 2-OH-phenyl Cl H C₂H₅ 1023  3-OH-phenyl Cl H C₂H₅ 1024  4-OH-phenyl Cl HC₂H₅ 1025  2-OCH₃-phenyl Cl H C₂H₅ 1026  3-OCH₃-phenyl Cl H C₂H₅ 1027 4-OCH₃-phenyl Cl H C₂H₅ 1028  2-OCF₃-phenyl Cl H C₂H₅ 1029 3-OCF₃-phenyl Cl H C₂H₅ 1030  4-OCF₃-phenyl Cl H C₂H₅ 1031 2-OCHF₂-phenyl Cl H C₂H₅ 1032  3-OCHF₂-phenyl Cl H C₂H₅ 1033 4-OCHF₂-phenyl Cl H C₂H₅ 1034  2-CF₃-phenyl Cl H C₂H₅ 1035  3-CF₃-phenylCl H C₂H₅ 1036  4-CF₃-phenyl Cl H C₂H₅ 1037  2-CH₃-phenyl Cl H C₂H₅1038  3-CH₃-phenyl Cl H C₂H₅ 1039  4-CH₃-phenyl Cl H C₂H₅ 1040 2-NO₂-phenyl Cl H C₂H₅ 1041  3-NO₂-phenyl Cl H C₂H₅ 1042  4-NO₂-phenylCl H C₂H₅ 1043  2-pyridyl Cl H C₂H₅ 1044  3-pyridyl Cl H C₂H₅ 1045 4-pyridyl Cl H C₂H₅ 1046  cyclohexylamino Cl H C₂H₅ 1047 cyclopentylamino Cl H C₂H₅ 1046  CH₃ CH₃ CH₃ i-C₃H₇ 1049  C₂H₅ CH₃ CH₃i-C₃H₇ 1050  n-C₃H₇ CH₃ CH₃ i-C₃H₇ 1051  i-C₃H₇ CH₃ CH₃ i-C₃H₇ 1052 n-C₄H₉ CH₃ CH₃ i-C₃H₇ 1053  s-C₄H₉ CH₃ CH₃ i-C₃H₇ 1054  i-C₄H₉ CH₃ CH₃i-C₃H₇ 1055  t-C₄H₉ CH₃ CH₃ i-C₃H₇ 1056  CH₂Cl CH₃ CH₃ i-C₃H₇ 1057 CHCl₂ CH₃ CH₃ i-C₃H₇ 1058  CCl₃ CH₃ CH₃ i-C₃H₇ 1059  CH₂F CH₃ CH₃ i-C₃H₇1060  CHF₂ CH₃ CH₃ i-C₃H₇ 1061  CF₃ CH₃ CH₃ i-C₃H₇ 1062  CH₂CF₃ CH₃ CH₃i-C₃H₇ 1063  CH₂OCH₃ CH₃ CH₃ i-C₃H₇ 1064  CH₂OCH₂CH₃ CH₃ CH₃ i-C₃H₇1065  CH₂NH₂ CH₃ CH₃ i-C₃H₇ 1066  (CH₂)₂COCH₃ CH₃ CH₃ i-C₃H₇ 1067 phenyl CH₃ CH₃ i-C₃H₇ 1068  2-F-phenyl CH₃ CH₃ i-C₃H₇ 1069  3-F-phenylCH₃ CH₃ i-C₃H₇ 1070  4-F-phenyl CH₃ CH₃ i-C₃H₇ 1071  2-Cl-phenyl CH₃ CH₃i-C₃H₇ 1072  3-Cl-phenyl CH₃ CH₃ i-C₃H₇ 1073  4-Cl-phenyl CH₃ CH₃ i-C₃H₇1074  2-OH-phenyl CH₃ CH₃ i-C₃H₇ 1075  3-OH-phenyl CH₃ CH₃ i-C₃H₇ 1076 4-OH-phenyl CH₃ CH₃ i-C₃H₇ 1077  2-OCH₃-phenyl CH₃ CH₃ i-C₃H₇ 1078 3-OCH₃-phenyl CH₃ CH₃ i-C₃H₇ 1079  4-OCH₃-phenyl CH₃ CH₃ i-C₃H₇ 1080 2-OCF₃-phenyl CH₃ CH₃ i-C₃H₇ 1081  3-OCF₃-phenyl CH₃ CH₃ i-C₃H₇ 1082 4-OCF₃-phenyl CH₃ CH₃ i-C₃H₇ 1083  2-OCHF₂-phenyl CH₃ CH₃ i-C₃H₇ 1084 3-OCHF₂-phenyl CH₃ CH₃ i-C₃H₇ 1085  4-OCHF₂-phenyl CH₃ CH₃ i-C₃H₇ 1086 2-CF₃-phenyl CH₃ CH₃ i-C₃H₇ 1087  3-CF₃-phenyl CH₃ CH₃ i-C₃H₇ 1088 4-CF₃-phenyl CH₃ CH₃ i-C₃H₇ 1089  2-CH₃-phenyl CH₃ CH₃ i-C₃H₇ 1090 3-CH₃-phenyl CH₃ CH₃ i-C₃H₇ 1091  4-CH₃-phenyl CH₃ CH₃ i-C₃H₇ 1092 2-NO₂-phenyl CH₃ CH₃ i-C₃H₇ 1093  3-NO₂-phenyl CH₃ CH₃ i-C₃H₇ 1094 4-NO₂-phenyl CH₃ CH₃ i-C₃H₇ 1095  2-pyridyl CH₃ CH₃ i-C₃H₇ 1096 3-pyridyl CH₃ CH₃ i-C₃H₇ 1097  4-pyridyl CH₃ CH₃ i-C₃H₇ 1098 cyclohexylamino CH₃ CH₃ i-C₃H₇ 1099  cyclopentylamino CH₃ CH₃ i-C₃H₇1100  H OCH₃ CH₃ i-C₃H₇ 1101  CH₃ OCH₃ CH₃ i-C₃H₇ 1102  C₂H₅ OCH₃ CH₃i-C₃H₇ 1103  n-C₃H₇ OCH₃ CH₃ i-C₃H₇ 1104  i-C₃H₇ OCH₃ CH₃ i-C₃H₇ 1105 n-C₄H₉ OCH₃ CH₃ i-C₃H₇ 1106  s-C₄H₉ OCH₃ CH₃ i-C₃H₇ 1107  i-C₄H₉ OCH₃CH₃ i-C₃H₇ 1108  t-C₄H₉ OCH₃ CH₃ i-C₃H₇ 1109  CH₂Cl OCH₃ CH₃ i-C₃H₇1110  CHCl₂ OCH₃ CH₃ i-C₃H₇ 1111  CCl₃ OCH₃ CH₃ i-C₃H₇ 1112  CH₂F OCH₃CH₃ i-C₃H₇ 1113  CHF₂ OCH₃ CH₃ i-C₃H₇ 1114  CF₃ OCH₃ CH₃ i-C₃H₇ 1115 CH₂CF₃ OCH₃ CH₃ i-C₃H₇ 1116  CH₂OCH₃ OCH₃ CH₃ i-C₃H₇ 1117  CH₂OCH₂CH₃OCH₃ CH₃ i-C₃H₇ 1118  CH₂NH₂ OCH₃ CH₃ i-C₃H₇ 1119  (CH₂)₂COCH₃ OCH₃ CH₃i-C₃H₇ 1120  phenyl OCH₃ CH₃ i-C₃H₇ 1121  2-F-phenyl OCH₃ CH₃ i-C₃H₇1122  3-F-phenyl OCH₃ CH₃ i-C₃H₇ 1123  4-F-phenyl OCH₃ CH₃ i-C₃H₇ 1124 2-Cl-phenyl OCH₃ CH₃ i-C₃H₇ 1125  3-Cl-phenyl OCH₃ CH₃ i-C₃H₇ 1126 4-Cl-phenyl OCH₃ CH₃ i-C₃H₇ 1127  2-OH-phenyl OCH₃ CH₃ i-C₃H₇ 1128 3-OH-phenyl OCH₃ CH₃ i-C₃H₇ 1129  4-OH-phenyl OCH₃ CH₃ i-C₃H₇ 1130 2-OCH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1131  3-OCH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1132 4-OCH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1133  2-OCF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1134 3-OCF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1135  4-OCF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1136 2-OCHF₂-phenyl OCH₃ CH₃ i-C₃H₇ 1137  3-OCHF₂-phenyl OCH₃ CH₃ i-C₃H₇1138  4-OCHF₂-phenyl OCH₃ CH₃ i-C₃H₇ 1139  2-CF₃-phenyl OCH₃ CH₃ i-C₃H₇1140  3-CF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1141  4-CF₃-phenyl OCH₃ CH₃ i-C₃H₇1142  2-CH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1143  3-CH₃-phenyl OCH₃ CH₃ i-C₃H₇1144  4-CH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1145  2-NO₂-phenyl OCH₃ CH₃ i-C₃H₇1146  3-NO₂-phenyl OCH₃ CH₃ i-C₃H₇ 1147  4-NO₂-phenyl OCH₃ CH₃ i-C₃H₇1148  2-pyridyl OCH₃ CH₃ i-C₃H₇ 1149  3-pyridyl OCH₃ CH₃ i-C₃H₇ 1150 4-pyridyl OCH₃ CH₃ i-C₃H₇ 1151  cyclohexylamino OCH₃ CH₃ i-C₃H₇ 1152 cyclopentylamino OCH₃ CH₃ i-C₃H₇ 1153  H Cl CH₃ i-C₃H₇ 1154  CH₃ Cl CH₃i-C₃H₇ 1155  C₂H₅ Cl CH₃ i-C₃H₇ 1156  n-C₃H₇ Cl CH₃ i-C₃H₇ 1157  i-C₃H₇Cl CH₃ i-C₃H₇ 1158  n-C₄H₉ Cl CH₃ i-C₃H₇ 1159  s-C₄H₉ Cl CH₃ i-C₃H₇1160  i-C₄H₉ Cl CH₃ i-C₃H₇ 1161  t-C₄H₉ Cl CH₃ i-C₃H₇ 1162  CH₂Cl Cl CH₃i-C₃H₇ 1163  CHCl₂ Cl CH₃ i-C₃H₇ 1164  CCl₃ Cl CH₃ i-C₃H₇ 1165  CH₂F ClCH₃ i-C₃H₇ 1166  CHF₂ Cl CH₃ i-C₃H₇ 1167  CF₃ Cl CH₃ i-C₃H₇ 1168  CH₂CF₃Cl CH₃ i-C₃H₇ 1169  CH₂OCH₃ Cl CH₃ i-C₃H₇ 1170  CH₂OCH₂CH₃ Cl CH₃ i-C₃H₇1171  CH₂NH₂ Cl CH₃ i-C₃H₇ 1172  (CH₂)₂COCH₃ Cl CH₃ i-C₃H₇ 1173  phenylCl CH₃ i-C₃H₇ 1174  2-F-phenyl Cl CH₃ i-C₃H₇ 1175  3-F-phenyl Cl CH₃i-C₃H₇ 1176  4-F-phenyl Cl CH₃ i-C₃H₇ 1177  2-Cl-phenyl Cl CH₃ i-C₃H₇1178  3-Cl-phenyl Cl CH₃ i-C₃H₇ 1179  4-Cl-phenyl Cl CH₃ i-C₃H₇ 1180 2-OH-phenyl Cl CH₃ i-C₃H₇ 1181  3-OH-phenyl Cl CH₃ i-C₃H₇ 1182 4-OH-phenyl Cl CH₃ i-C₃H₇ 1183  2-OCH₃-phenyl Cl CH₃ i-C₃H₇ 1184 3-OCH₃-phenyl Cl CH₃ i-C₃H₇ 1185  4-OCH₃-phenyl Cl CH₃ i-C₃H₇ 1186 2-OCF₃-phenyl Cl CH₃ i-C₃H₇ 1187  3-OCF₃-phenyl Cl CH₃ i-C₃H₇ 1188 4-OCF₃-phenyl Cl CH₃ i-C₃H₇ 1189  2-OCHF₂-phenyl Cl CH₃ i-C₃H₇ 1190 3-OCHF₂-phenyl Cl CH₃ i-C₃H₇ 1191  4-OCHF₂-phenyl Cl CH₃ i-C₃H₇ 1192 2-CF₃-phenyl Cl CH₃ i-C₃H₇ 1193  3-CF₃-phenyl Cl CH₃ i-C₃H₇ 1194 4-CF₃-phenyl Cl CH₃ i-C₃H₇ 1195  2-CH₃-phenyl Cl CH₃ i-C₃H₇ 1196 3-CH₃-phenyl Cl CH₃ i-C₃H₇ 1197  4-CH₃-phenyl Cl CH₃ i-C₃H₇ 1198 2-NO₂-phenyl Cl CH₃ i-C₃H₇ 1199  3-NO₂-phenyl Cl CH₃ i-C₃H₇ 1200 4-NO₂-phenyl Cl CH₃ i-C₃H₇ 1201  2-pyridyl Cl CH₃ i-C₃H₇ 1202  3-pyridylCl CH₃ i-C₃H₇ 1203  4-pyridyl Cl CH₃ i-C₃H₇ 1204  cyclohexylamino Cl CH₃i-C₃H₇ 1205  cyclopentylamino Cl CH₃ i-C₃H₇ 1206  CH₃ CH₃ H i-C₃H₇ 1207 C₂H₅ CH₃ H i-C₃H₇ 1208  n-C₃H₇ CH₃ H i-C₃H₇ 1209  i-C₃H₇ CH₃ H i-C₃H₇1210  n-C₄H₉ CH₃ H i-C₃H₇ 1211  s-C₄H₉ CH₃ H i-C₃H₇ 1212  i-C₄H₉ CH₃ Hi-C₃H₇ 1213  t-C₄H₉ CH₃ H i-C₃H₇ 1214  CH₂Cl CH₃ H i-C₃H₇ 1215  CHCl₂CH₃ H i-C₃H₇ 1116  CCl₃ CH₃ H i-C₃H₇ 1217  CH₂F CH₃ H i-C₃H₇ 1218  CHF₂CH₃ H i-C₃H₇ 1219  CF₃ CH₃ H i-C₃H₇ 1220  CH₂CF₃ CH₃ H i-C₃H₇ 1221 CH₂OCH₃ CH₃ H i-C₃H₇ 1222  CH₂OCH₂CH₃ CH₃ H i-C₃H₇ 1223  CH₂NH₂ CH₃ Hi-C₃H₇ 1224  (CH₂)₂COCH₃ CH₃ H i-C₃H₇ 1225  phenyl CH₃ H i-C₃H₇ 1226 2-F-phenyl CH₃ H i-C₃H₇ 1227  3-F-phenyl CH₃ H i-C₃H₇ 1228  4-F-phenylCH₃ H i-C₃H₇ 1229  2-Cl-phenyl CH₃ H i-C₃H₇ 1230  3-Cl-phenyl CH₃ Hi-C₃H₇ 1231  4-Cl-phenyl CH₃ H i-C₃H₇ 1232  2-OH-phenyl CH₃ H i-C₃H₇1233  3-OH-phenyl CH₃ H i-C₃H₇ 1234  4-OH-phenyl CH₃ H i-C₃H₇ 1235 2-OCH₃-phenyl CH₃ H i-C₃H₇ 1236  3-OCH₃-phenyl CH₃ H i-C₃H₇ 1237 4-OCH₃-phenyl CH₃ H i-C₃H₇ 1238  2-OCF₃-phenyl CH₃ H i-C₃H₇ 1239 3-OCF₃-phenyl CH₃ H i-C₃H₇ 1240  4-OCF₃-phenyl CH₃ H i-C₃H₇ 1241 2-OCHF₂-phenyl CH₃ H i-C₃H₇ 1242  3-OCHF₂-phenyl CH₃ H i-C₃H₇ 1243 4-OCHF₂-phenyl CH₃ H i-C₃H₇ 1244  2-CF₃-phenyl CH₃ H i-C₃H₇ 1245 3-CF₃-phenyl CH₃ H i-C₃H₇ 1246  4-CF₃-phenyl CH₃ H i-C₃H₇ 1247 2-CH₃-phenyl CH₃ H i-C₃H₇ 1248  3-CH₃-phenyl CH₃ H i-C₃H₇ 1249 4-CH₃-phenyl CH₃ H i-C₃H₇ 1250  2-NO₂-phenyl CH₃ H i-C₃H₇ 1251 3-NO₂-phenyl CH₃ H i-C₃H₇ 1252  4-NO₂-phenyl CH₃ H i-C₃H₇ 1253 2-pyridyl CH₃ H i-C₃H₇ 1254  3-pyridyl CH₃ H i-C₃H₇ 1255  4-pyridyl CH₃H i-C₃H₇ 1256  cyclohexylamino CH₃ H i-C₃H₇ 1257  cyclopentylamino CH₃ Hi-C₃H₇ 1258  H OCH₃ H i-C₃H₇ 1259  CH₃ OCH₃ H i-C₃H₇ 1260  C₂H₅ OCH₃ Hi-C₃H₇ 1261  n-C₃H₇ OCH₃ H i-C₃H₇ 1262  i-C₃H₇ OCH₃ H i-C₃H₇ 1263 n-C₄H₉ OCH₃ H i-C₃H₇ 1264  s-C₄H₉ OCH₃ H i-C₃H₇ 1265  i-C₄H₉ OCH₃ Hi-C₃H₇ 1266  t-C₄H₉ OCH₃ H i-C₃H₇ 1267  CH₂Cl OCH₃ H i-C₃H₇ 1268  CHCl₂OCH₃ H i-C₃H₇ 1269  CCl₃ OCH₃ H i-C₃H₇ 1270  CH₂F OCH₃ H i-C₃H₇ 1271 CHF₂ OCH₃ H i-C₃H₇ 1272  CF₃ OCH₃ H i-C₃H₇ 1273  CH₂CF₃ OCH₃ H i-C₃H₇1274  CH₂OCH₃ OCH₃ H i-C₃H₇ 1275  CH₂OCH₂CH₃ OCH₃ H i-C₃H₇ 1276  CH₂NH₂OCH₃ H i-C₃H₇ 1277  (CH₂)₂COCH₃ OCH₃ H i-C₃H₇ 1278  phenyl OCH₃ H i-C₃H₇1279  2-F-phenyl OCH₃ H i-C₃H₇ 1280  3-F-phenyl OCH₃ H i-C₃H₇ 1281 4-F-phenyl OCH₃ H i-C₃H₇ 1282  2-Cl-phenyl OCH₃ H i-C₃H₇ 1283 3-Cl-phenyl OCH₃ H i-C₃H₇ 1284  4-Cl-phenyl OCH₃ H i-C₃H₇ 1285 2-OH-phenyl OCH₃ H i-C₃H₇ 1286  3-OH-phenyl OCH₃ H i-C₃H₇ 1287 4-OH-phenyl OCH₃ H i-C₃H₇ 1288  2-OCH₃-phenyl OCH₃ H i-C₃H₇ 1289 3-OCH₃-phenyl OCH₃ H i-C₃H₇ 1290  4-OCH₃-phenyl OCH₃ H i-C₃H₇ 1291 2-OCF₃-phenyl OCH₃ H i-C₃H₇ 1292  3-OCF₃-phenyl OCH₃ H i-C₃H₇ 1293 4-OCF₃-phenyl OCH₃ H i-C₃H₇ 1294  2-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1295 3-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1296  4-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1297 2-CF₃-phenyl OCH₃ H i-C₃H₇ 1298  3-CF₃-phenyl OCH₃ H i-C₃H₇ 1299 4-CF₃-phenyl OCH₃ H i-C₃H₇ 1300  2-CH₃-phenyl OCH₃ H i-C₃H₇ 1301 3-CH₃-phenyl OCH₃ H i-C₃H₇ 1302  4-CH₃-phenyl OCH₃ H i-C₃H₇ 1303 2-NO₂-phenyl OCH₃ H i-C₃H₇ 1304  3-NO₂-phenyl OCH₃ H i-C₃H₇ 1305 4-NO₂-phenyl OCH₃ H i-C₃H₇ 1306  2-pyridyl OCH₃ H i-C₃H₇ 1307  3-pyridylOCH₃ H i-C₃H₇ 1308  4-pyridyl OCH₃ H i-C₃H₇ 1309  cyclohexylamino OCH₃ Hi-C₃H₇ 1310  cyclopentylamino OCH₃ H i-C₃H₇ 1311  H Cl H i-C₃H₇ 1312 CH₃ Cl H i-C₃H₇ 1313  C₂H₅ Cl H i-C₃H₇ 1314  n-C₃H₇ Cl H i-C₃H₇ 1315 i-C₃H₇ Cl H i-C₃H₇ 1316  n-C₄H₉ Cl H i-C₃H₇ 1317  s-C₄H₉ Cl H i-C₃H₇1318  i-C₄H₉ Cl H i-C₃H₇ 1319  t-C₄H₉ Cl H i-C₃H₇ 1320  CH₂Cl Cl Hi-C₃H₇ 1321  CHCl₂ Cl H i-C₃H₇ 1322  CH₃ Cl H i-C₃H₇ 1323  CH₂F Cl Hi-C₃H₇ 1324  CHF₂ Cl H i-C₃H₇ 1325  CF₃ Cl H i-C₃H₇ 1326  CH₂CF₃ Cl Hi-C₃H₇ 1327  CH₂OCH₃ Cl H i-C₃H₇ 1328  CH₂OCH₂CH₃ Cl H i-C₃H₇ 1329 CH₂NH₂ Cl H i-C₃H₇ 1330  (CH₂)₂COCH₃ Cl H i-C₃H₇ 1331  phenyl Cl Hi-C₃H₇ 1332  2-F-phenyl Cl H i-C₃H₇ 1333  3-F-phenyl Cl H i-C₃H₇ 1334 4-F-phenyl Cl H i-C₃H₇ 1335  2-Cl-phenyl Cl H i-C₃H₇ 1336  3-Cl-phenylCl H i-C₃H₇ 1337  4-Cl-phenyl Cl H i-C₃H₇ 1338  2-OH-phenyl Cl H i-C₃H₇1339  3-OH-phenyl Cl H i-C₃H₇ 1340  4-OH-phenyl Cl H i-C₃H₇ 1341 2-OCH₃-phenyl Cl H i-C₃H₇ 1342  3-OCH₃-phenyl Cl H i-C₃H₇ 1343 4-OCH₃-phenyl Cl H i-C₃H₇ 1344  2-OCF₃-phenyl Cl H i-C₃H₇ 1345 3-OCF₃-phenyl OCH₃ H i-C₃H₇ 1346  4-OCF₃-phenyl OCH₃ H i-C₃H₇ 1347 2-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1348  3-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1349 4-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1350  2-CF₃-phenyl OCH₃ H i-C₃H₇ 1351 3-CF₃-phenyl OCH₃ H i-C₃H₇ 1352  4-CF₃-phenyl OCH₃ H i-C₃H₇ 1353 2-CH₃-phenyl OCH₃ H i-C₃H₇ 1353  3-CH₃-phenyl OCH₃ H i-C₃H₇ 1354 4-CH₃-phenyl OCH₃ H i-C₃H₇ 1355  H CH₃ H H 1356  3-NO₂-phenyl OCH₃ Hi-C₃H₇ 1357  H CH₃ CH₃ CH₃ 1358  2-pyridyl OCH₃ H i-C₃H₇ 1359  H CH₃ CH₃C₂H₅ 1360  H CH₃ H C₂H₅ 1361  H CH₃ CH₃ i-C₃H₇ 1362  H CH₃ H i-C₃H₇1363  H CH₃ H CH₃

Examples of benzimidazol-5-ylcarbonyl derivatives of cyclohexenones(compounds I-3=compounds I where X=C—R³ and Y=N—R⁴) particularlypreferred according to the invention are the compounds listed in Tables51 to 75.

TABLE 51 Compounds I-3a.1 to I-3a.1363 I-3a

Compounds of the formula I-3a, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 52 Compounds I-3b.1 to I-3b.1363 I-3b

Compounds of the formula I-3b, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 53 Compounds I-3c.1 to I-3c.1363 I-3c

Compounds of the formula I-3c, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 54 Compounds I-3d.1 to I-3d.1363 I-3d

Compounds of the formula I-3d, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 55 Compounds I-3e.1 to I-3e.1363 I-3e

Compounds of the formula I-3e, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 56 Compounds I-3f.1 to I-3f.1363 I-3f

Compounds of the formula I-3f, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 57 Compounds I-3g.1 to I-3g.1363 I-3g

Compounds of the formula I-3g, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 58 Compounds I-3h.1 to I-3h.1363 I-3h

Compounds of the formula I-3h, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 59 Compounds I-3i.1 to I-3i.1363 I-3i

Compounds of the formula I-3i, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 60 Compounds I-3k.1 to I-3k.1363 I-3k

Compounds of the formula I-3k, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 61 Compounds I-3l.1 to I-3l.1363 I-3l

Compounds of the formula I-31, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 62 Compounds I-3m.1 to I-3m.1363 I-3m

Compounds of the formula I-3m, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 63 Compounds I-3n.1 to I-3n.1363 I-3n

Compounds of the formula I-3n, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 64 Compounds I-3o.1 to I-3o.1363 I-3o

Compounds of the formula I-3o, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 65 Compounds I-3p.1 to I-3p.1363 I-3p

Compounds of the formula I-3p, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 66 Compounds I-3q.1 to I-3q.1363 I-3q

Compounds of the formula-I-3q, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 67 Compounds I-3r.1 to I-3r.1363 I-3r

Compounds of the formula I-3r, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 68 Compounds I-3s.1 to I-3s.1363 I-3s

Compounds of the formula I-3s, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 69 Compounds I-3t.1 to I-3t.1363 I-3t

Compounds of the formula I-3t, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 70 Compounds I-3u.1 to I-3u.1363 I-3u

Compounds of the formula I-3u, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 71 Compounds I-3v.1 to I-3v.1363 I-3v

Compounds of the formula I-3v, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 72 Compounds I-3w.1 to I-3w.1363 I-3w

Compounds of the formula I-3w, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 73 Compounds I-3x.1 to I-3x.1363 I-3x

Compounds of the formula I-3x, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 74 Compounds I-3y.1 to I-3y.1363 I-3y

Compounds of the formula I-3y, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE 75 Compounds I-3z.1 to I-3z.1363 I-3z

Compounds of the formula I-3z, in which the substituents R¹, R², R³ andR⁴ for each individual compound correspond in each case to one row ofTable B.

TABLE C R¹ R² X Y 1 H H N S 2 CH₃ H N S 3 Cl H N S 4 OCH₃ H N S 5 SCH₃ HN S 6 S(O)₂CH₃ H N S 7 H Cl N S 8 CH₃ Cl N S 9 Cl Cl N S 10 OCH₃ Cl N S11 SCH₃ Cl N S 12 S(O)₂CH₃ Cl N S 13 H CH₃ N S 14 CH₃ CH₃ N S 15 Cl CH₃N S 16 OCH₃ CH₃ N S 17 SCH₃ CH₃ N S 18 S(O)₂CH₃ CH₃ N S 19 H H N NH 20CH₃ H N NH 21 Cl H N NH 22 OCH₃ H N NH 23 SCH₃ H N NH 24 S(O)₂CH₃ H N NH25 H Cl N NH 26 CH₃ Cl N NH 27 Cl Cl N NH 28 OCH₃ Cl N NH 29 SCH₃ Cl NNH 30 S(O)₂CH₃ Cl N NH 31 H CH₃ N NH 32 CH₃ CH₃ N NH 33 Cl CH₃ N NH 34OCH₃ CH₃ N NH 35 SCH₃ CH₃ N NH 36 S(O)₂CH₃ CH₃ N NH 37 H H N NCH₃ 38 CH₃H N NCH₃ 39 Cl H N NCH₃ 40 OCH₃ H N NCH₃ 41 SCH₃ H N NCH₃ 42 S(O)₂CH₃ HN NCH₃ 43 H Cl N NCH₃ 44 CH₃ Cl N NCH₃ 45 Cl Cl N NCH₃ 46 OCH₃ Cl N NCH₃47 SCH₃ Cl N NCH₃ 48 S(O)₂CH₃ Cl N NCH₃ 49 H CH₃ N NCH₃ 50 CH₃ CH₃ NNCH₃ 51 Cl CH₃ N NCH₃ 52 OCH₃ CH₃ N NCH₃ 53 SCH₃ CH₃ N NCH₃ 54 S(O)₂CH₃CH₃ N NCH₃ 55 H H N NC₂H₅ 56 CH₃ H N NC₂H₅ 57 Cl H N NC₂H₅ 58 OCH₃ H NNC₂H₅ 59 SCH₃ H N NC₂H₅ 60 S(O)₂CH₃ H N NC₂H₅ 61 H Cl N NC₂H₅ 62 CH₃ ClN NC₂H₅ 63 Cl Cl N NC₂H₅ 64 OCH₃ Cl N NC₂H₅ 65 SCH₃ Cl N NC₂H₅ 66S(O)₂CH₃ Cl N NC₂H₅ 67 H CH₃ N NC₂H₅ 68 CH₃ CH₃ N NC₂H₅ 69 Cl CH₃ NNC₂H₅ 70 OCH₃ CH₃ N NC₂H₅ 71 SCH₃ CH₃ N NC₂H₅ 72 S(O)₂CH₃ CH₃ N NC₂H₅ 73H H N N-i-C₃H₇ 74 CH₃ H N N-i-C₃H₇ 75 Cl H N N-i-C₃H₇ 76 OCH₃ H NN-i-C₃H₇ 77 SCH₃ H N N-i-C₃H₇ 78 S(O)₂CH₃ H N N-i-C₃H₇ 79 H Cl NN-i-C₃H₇ 80 CH₃ Cl N N-i-C₃H₇ 81 Cl Cl N N-i-C₃H₇ 82 OCH₃ Cl N N-i-C₃H₇83 SCH₃ Cl N N-i-C₃H₇ 84 S(O)₂CH₃ Cl N N-i-C₃H₇ 85 H CH₃ N N-i-C₃H₇ 86CH₃ CH₃ N N-i-C₃H₇ 87 Cl CH₃ N N-i-C₃H₇ 88 OCH₃ CH₃ N N-i-C₃H₇ 89 SCH₃CH₃ N N-i-C₃H₇ 90 S(O)₂CH₃ CH₃ N N-i-C₃H₇

Other examples of benzothiadiazol-5-ylcarbonyl derivatives ofcyclohexenones (X=N, Y=S) and benzotriazol-5-ylcarbonyl derivatives ofcyclohexenones (X=N, Y=N—R⁴) which are preferred according to theinvention are the compounds listed in Tables 76 to 100 (compounds I-4).

TABLE 76 Compounds I-4a.1 to I-4a.90 I-4a

Compounds of the formula I-4a, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 77 Compounds I-4b.1 to I-4b.90 I-4b

Compounds of the formula I-4b, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 78 Compounds I-4c.1 to I-4c.90 I-4c

Compounds of the formula I-4c, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 79 Compounds I-4d.1 to I-4d.90 I-4d

Compounds of the formula I-4d, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 80 Compounds I-4e.1 to I-4e.90 I-4e

Compounds of the formula I-4e, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 81 Compounds I-4f.1 to I-4f.90 I-4f

Compounds of the formula I-4f, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 82 Compounds I-4g.1 to I-4g.90 I-4g

Compounds of the formula I-4g, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 83 Compounds I-4h.1 to I-4h.90 I-4h

Compounds of the formula I-4h, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 84 Compounds I-4i.1 to I-4i.90 I-4i

Compounds of the formula I-4i, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 85 Compounds I-4k.1 to I-4k.90 I-4k

Compounds of the formula I-4k, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 86 Compounds I-4l.1 to I-4l.90 I-4l

Compounds of the formula I-4i, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 87 Compounds I-4m.1 to I-4m.90 I-4m

Compounds of the formula I-4m, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 88 Compounds I-4n.1 to I-4n.90 I-4n

Compounds of the formula I-4n, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 89 Compounds I-4o.1 to I-4o.90 I-4o

Compounds of the formula I-4o, in which the substituents R¹, R², X and Yfor each individual compound corresponding each case to one row of TableC.

TABLE 90 Compounds I-4p.1 to I-4p.90 I-4p

Compounds of the formula I-4p, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 91 Compounds I-4q.1 to I-4q.90 I-4q

Compounds of the formula I-4q, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 92 Compounds I-4r.1 to I-4r.90 I-4r

Compounds of the formula I-4r, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 93 Compounds I-4s.1 to I-4s.90 I-4s

Compounds of the formula I-4s, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 94 Compounds I-4t.1 to I-4t.90 I-4t

Compounds of the formula I-4t, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 95 Compounds I-4u.1 to I-4u.90 I-4u

Compounds of the formula I-4u, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 96 Compounds I-4v.1 to I-4v.90 I-4v

Compounds of the formula I-4v, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 97 Compounds I-4w.1 to I-4w.90 I-4w

Compounds of the formula I-4w, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 98 Compounds I-4x.1 to I-4x.90 I-4x

Compounds of the formula I-4x, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 99 Compounds I-4y.1 to I-4y.90 I-4y

Compounds of the formula I-4y, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

TABLE 100 Compounds I-4z.1 to I-4z.90 I-4z

Compounds of the formula I-4z, in which the substituents R¹, R², X and Yfor each individual compound correspond in each case to one row of TableC.

Compounds of the formula I where R⁸ is hydroxyl are prepared by reactingan activated carboxylic acid IVb or a carboxylic acid IVa, which ispreferably activated in situ, with a cyclohexane-1,3-dione of theformula III to give the acylation product, followed by rearrangement.

L¹ is a nucleophilically displaceable leaving group, such as halogen,for example bromine or chlorine, hetaryl, for example imidazolyl orpyridyl, carboxylate, for example acetate or trifluoroacetate, etc.

The activated carboxylic acid IVa can be employed directly, such as inthe case of the benzoyl halides, or be generated in situ, for exampleusing a carbodiimide, such asethyl-(3′-dimethylaminopropyl)carbodiimide, dicyclohexylcarbodiimide,triphenylphosphine/azodicarboxylic ester, 2-pyridinedisulfide/triphenylphosphine, carbonyldiimidazole, etc.

If appropriate, it may be advantageous to carry out the acylationreaction in the presence of a base. Here, the reactants and theauxiliary base are advantageously employed in equimolar amounts. In somecases, it may be advantageous to employ a slight excess of the auxiliarybase, for example from 1.2 to 1.5 molar equivalents, based on IVa orIVb.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkalimetal carbonates. Suitable solvents are, for example, chlorinatedhydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatichydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane,polar aprotic solvents, such as acetonitrile, dimethylformamide ordimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures ofthese.

If the activated carboxylic acid component used is a halide, it may beadvantageous to cool the reaction mixture to 0-10° C. when adding thisreactant. The mixture is subsequently stirred at 20-100° C., preferablyat 25-50° C., until the reaction has gone to completion. Work-up iscarried out in a customary manner, for example by pouring the reactionmixture into water and extracting the product of value. Solvents whichare suitable for this purpose are, in particular, methylene chloride,diethyl ether and ethyl acetate. After the organic phase has been driedand the solvent has been removed, the crude ester can be employed forthe rearrangement without further purification.

The rearrangement of the esters to give the compounds of the formula Iis advantageously carried out at 20-100° C. in a solvent and in thepresence of a base and, if appropriate, using a cyano compound ascatalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride,1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures ofthese. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine, aromaticamines, such as pyridine, or alkali metal carbonates, such as sodiumcarbonate or potassium carbonate, which are preferably employed in anequimolar amount or an up.to 4-fold excess, based on the ester.Preference is given to using triethylamine or alkali metal carbonate,preferably in twice the equimolar amount, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanideor potassium cyanide, and organic cyano compounds, such asacetonecyanohydrin or trimethylsilyl cyanide. They are employed in anamount of 1-50 mol percent, based on the ester. Preference is given tousing acetonecyanohydrin or trimethylsilyl cyanide, for example in anamount of 5-15, preferably about 10 mol percent, based on the ester.

Work-up can be carried out in a manner known per se. The reactionmixture is, for example, acidified with dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, and extracted with anorganic solvent, for example methylene chloride or ethyl acetate. Theorganic extract can be extracted with 5-10% strength alkali metalcarbonate solution, for example sodium carbonate or potassium carbonatesolution. The aqueous phase is acidified and the precipitate that isformed is filtered off with suction and/or extracted with methylenechloride or ethyl acetate, dried and concentrated.

B. Preparation of compounds of the formula I where R⁸=halogen is carriedout by reacting cyclohexenone derivatives of the formula I (whereR⁸=hydroxyl) with halogenating agents:

Here and below, “compound Ia” is a compound of the formula I where hexis a radical of the formula IIa and, correspondingly, compound Ib is acompound of the formula I where hex is a radical IIb.

Suitable halogenating agents are,for example, phosgene, diphosgene,triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride,phosphorus pentachloride, mesyl chloride,chloromethylene-N,N-dimethylammonium chloride, oxalyl bromide,phosphorus oxybromide, etc.

C. Compounds of the formula I where R⁸=OR¹⁵, OSO₂R¹⁶, OPOR¹⁷R¹² orOPSR¹⁷R¹⁸ are prepared by reacting cyclohexenone derivatives of theformula I (where R⁸=hydroxyl) with alkylating, sulfonylating orphosphonylating agents Vα, Vβ, Vγ and Vδb, respectively.

L² is a nucleophilically displaceable leaving group, such as halogen,for example chlorine or bromine, hetaryl, for example imidazolyl,carboxylate, for example aceate, or sulfonate, for example mesylate ortriflate, etc.

Compounds of the formula Vα, Vβ, Vγ or Vδ can be employed directly, suchas in the case of the carbonyl halides, or be generated in situ, forexample activated carboxylic acids (using carboxylic acid anddicyclohexylcarbodiimide, etc.).

D. Compounds of the formula I where R⁸=OR¹⁵, SR¹⁵, POR¹⁷R¹⁸, NR¹⁹R²⁰,ONR¹⁹R²⁰ or N-bonded heterocyclyl are prepared by reacting compounds ofthe formula I where R⁸=halogen, OSO₂R¹⁶ with compounds of the formulaVIα, VIβ, VIγ, VIδ, VIε or VIη, if appropriate in the presence of a baseor with prior formation of salt.

E. Compounds of the formula I where R⁸=SOR¹⁶, SO₂R¹⁶ are prepared, forexample, by reacting compounds of the formula I where R⁸=SR¹⁶ with anoxidizing agent.

Suitable oxidizing agents are, for example, m-chloroperbenzoic acid,peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, ifappropriate in the presence of a.catalyst, such as tungstate.

For the reactions mentioned under points B to E, the followingconditions apply:

The starting materials are.generally employed in equimolar amounts.However, it may also be advantageous to employ an excess of one or theother component.

If appropriate, it may be advantageous to carry out the reactions in thepresence of a base. Reactants and base are advantageously employed inequimolar amounts.

With respect to the processes C and D, it may, in certain cases, beadvantageous to employ an excess of base, for example 1.5 to 3 molarequivalents, in each case based on the starting material.

Suitable bases are tertiary alkylamines, such as triethylamine, aromaticamines, such as pyridine, alkali metal carbonates, for example sodiumcarbonate or potassium carbonate, alkali metal bicarbonates, such assodium bicarbonate and potassium bicarbonate, alkali metal alkoxides,such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, oralkali metal hydrides, for example sodium hydride. Preference is givento using triethylamine or pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene or chlorobenzene, ethers, such as diethyl ether,methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aproticsolvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide,or esters, such as ethyl acetate, or mixtures of these.

In general, the reaction temperature is in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to give the product.

Depending on the reaction conditions, in the processes B to D thecompounds Ia, Ib, or mixtures of these can be formed. The latter can beseparated by classic separation methods, for example crystallization,chromatography, etc.

The cyclohexanedions of the formula IV used as starting materials areknown or can be prepared by processes known per se (for example EP-A 71707, EP-A 142 741, EP-A 243 313, U.S. Pat. No. 4,249,937, WO 92/13821).

The alkylating agents Vα, sulfonylating agents Vβ, phosphonylatingagents Vγ and Vδ, and the compounds VIα, VIβ, VIγ, Vδ and VIε arelikewise known, or they can be prepared by known processes.

The carboxylic acids of the formula IVa and their activated derivativesIVb are either known from the literature, or they can be preparedanalogously to known processes.

Scheme 1 shows a customary route to benzothiazole-5-carboxylic acids(compounds IV-1).

In the formula IV-1, R is hydrogen (compound IV-1a) or a hydrocarbonradical which can be hydrolyzed, for example methyl (compound IV-1b).Compounds of the formula IV-1 can be prepared, for example, according toreaction step a) by condensation of ortho-aminothiophenols of theformula VIII (R′=H) or of ortho-aminothioethers of the formula VIII(R′=C₁-C₄-alkyl, for example methyl), using a carboxylic acid equivalent“R³—CO₂H” i.e. a carboxylic acid R³CO₂H or activated derivatives R³COL¹,R³C(L³)₃ thereof where L¹ is a reactive leaving group and L³ is aC₁-C₄-alkoxy group. Examples of L¹ are chlorine, bromine, carboxylate,such as acetate, trifluoroacetate, N-heterocyclyl, such as imidazolyl,pyridyl etc. Examples of R³COL¹ and R³C(L³)₃ are acyl halides,carboxylic esters and carboxylic anhydrides, and the ortho esters of thecarboxylic acids R³CO₂H.

The condensation reaction a) is preferably carried out under neutral toacidic reaction conditions, preferably in the presence of an inorganicor organic acid, for example hydrochloric acid, sulfuric acid,p-toluenesulfonic acid and pyridinium p-toluenesulfonate, in an organicsolvent at 0-150° C., preferably in the range from 20 to 120° C.Suitable solvents are, in particular, saturated hydrocarbons,halogenated hydrocarbons, aromatic hydrocarbons, such as benzene,aliphatic ethers, such as diethyl ether and tert-butyl methyl ether, orpyridine. For the preparation of benzothiazoles from o-aminothiophenolsor corresponding thiomethyl ethers, see also Houben-Weyl,-Methoden derOrganischen Chemie, Vol. E 8b, pp.869-871.

Step a) can also be carried out in two steps, by initially convertingthe amino function in VIII with a carboxylic acid R⁹—COOH or aderivative thereof into the carboxamide, which is subsequently cyclizedto give the benzothiazole of the formula IV-1.

The conversion into the amide is carried out under the conditions whichare customary for amide formation, for example by reacting an acid inthe presence of a water-binding agent. Cyclization is carried out withLewis acids or phosgene. In this case, the cyclization is preferablycarried out in an inert organic solvent, for example an aliphatic oraromatic hydrocarbon, or in a halogenated hydrocarbon.

According to Scheme 1, ortho-aminothiophenols of the formula VIII (R′=H)can be prepared starting with 3-nitrotoluenes of the formula IX. Themethyl group can be oxidized in a known manner, catalytically orstoichiometrically, to give the carboxylic acid (step b). Suitableoxidizing agents are, for example, metal oxides of transition metals,for example manganese dioxide, chromium trioxide and their anioniccomplex salts, for example sodium dichromate or chromyl chloride,pyridinium chromate, furthermore oxidizing acids, for example HNO₃,oxidizing gases, such as oxygen or chlorine, if appropriate in thepresence of transition metals (or salts thereof, for example oxides orchlorides) as catalysts. Depending on the solubility of the compound tobe oxidized and depending on the oxidizing agent used, the reaction ispreferably carried out in aqueous solutions, monophasic systems of waterand water-miscible organic solvents or in multiphasic systems of waterand organic solvents with phase-transfer catalysis. Depending on thechosen oxidizing agent, the oxidation is generally carried out in.therange from −15 to +150° C., preferably in the range from 0 to 100° C.For the oxidation of aromatic methyl.groups to benzoic acids, see, forexample, Houben-Weyl: “Methoden der organischen Chemie”, Vol. V, IV/1a,1981; Vol. VIII 1952; E. Bengtsson, Acta Chem. Scand. 7 (1953), 774;Singer et al., Org. Synth. Coll. Vol III, 1955, 740; B. A. S. Hay etal., Can. J. Chem. 43 (1965), 1306).

The resulting 3-nitrobenzoic acid derivatives are subsequently, in stepc), reduced to the 3-aminobenzoic acids. The selective reduction ofaromatic nitro groups in the presence of carboxylic acid groups is knownin principle. Suitable reducing agents are, for example, hydrazines,metal hydrides, such as aluminum hydride, and complex compounds derivedtherefrom, such as lithium aluminum hydride, diisobutylaluminum hydrideor boranes. The preferred reducing agent is hydrogen in the presence ofcatalytic amounts of transition metals, for example Ni, Pd, Pt, Ru orRh, which may be employed in supported form, for example on activecarbon, in the form of activated metals, for example Raney nickel, or inthe form of soluble complex compounds. Suitable solvents for thereduction are, depending on the solubility of the substrate to behydrogenated and the chosen reducing agent, C₁-C₄-alcohols, such asmethanol, ethanol, n-propanol, isopropanol or n-butanol, halogenatedC₁-C₆-hydrocarbons, such as dichloromethane, trichloromethane,trichloroethane, trichloroethylene, aromatic hydrocarbons, such asbenzene, toluene, xylenes, chlorobenzene, aqueous solutions of inorganicor organic acids, such as aqueous hydrochloric acid. The reduction isusually carried out in the range from −15 to +100° C., preferably in therange from 0 to 40° C. The reduction with hydrogen is usually carriedout at a hydrogen pressure in the range from 1 to 50 bar, preferably inthe range from 1 to 10 bar. For the catalytic hydrogenation of aromaticnitro groups, see, for example, Rylander in “Catalytic Hydrogenationover Platinum Metals”, Academic Press, New York, 1967, 168-202; Furst etal., Chem. Rev. 65 (1965), 52; Tepko et al., J. Org. Chem. 45 (1980),4992.

The resulting m-aminobenzoic acids of the formula Xa (R=H) are then, ina further reaction step d), reacted with an organic isothiocyanate (inscheme 1 methyl isothiocyanate) to give a substituted thioureaderivative which, without further isolation, is cyclized oxidatively togive the benzothiazole-5-carboxylic acid of the formula IX-1a (in scheme1 with R³=NH—CH₃).

The first reaction step in step d), i.e. the conversion of them-aminobenzoic acid of the formula Xa into the substituted urea iscarried out by reaction with a C₁-C₆-alkyl isothiocyanate or anunsubstituted or substituted phenyl isothiocyanate in an anhydrousorganic solvent at from −15° C. to 150° C., preferably in the range from−15° C. to 100° C. Suitable solvents are, for example, aliphatic orcycloaliphatic hydrocarbons, such as n-hexane or cyclohexane,halogenated hydrocarbons, such as dichloromethane, trichloromethane,trichloroethane, trichloroethylene, aromatic hydrocarbons, such asbenzene or anisole, dialkyl ethers or cyclic ethersi such as diethylether, methyl tert-butyl ether, tetrahydrofuran or dioxane, anhydrouscarboxylic acids, such as glacial acetic acid, or pyridine. For thepreparation of substituted thioureas see, for example: F. Kurzer, Org.Synth. 31 (1951), 21; R. R. Gupta et al., Synth. Commun. 17(2) (1987),229-240; Rathke, Ber. Dtsch. Chem. Ges. 18 (1885), 3102; Schiff, JustusLiebigs Ann. Chem. 148 (1868), 338; R. L. Frank, P. V. Smith, Org.Synth. III (1955), 735, N. B. Ambati et al., Synth. Commun. 27 (9)(1997), 1487-1493; W. O. Foye, J. Pharm. Sci. 66 (7) (1977), 923-926.

The resulting substituted thiourea derivative is then, in a secondreaction step of step d), cyclized using a halogen-containing oxidizingagent, such as bromine, sulfuryl chloride or chlorine in an inertorganic solvent, to give the substituted2-aminobenzothiazole-5-carboxylic acid of the general formula IV-1a (inscheme 1, R³ is NH—CH₃). The cyclization is generally carried out in therange from −15 to +150° C., preferably in the range from 0 to 120° C.Suitable solvents are, in particular, the abovementioned aliphatic orcycloaliphatic hydrocarbons, the abovementioned aromatic hydrocarbons,the abovementioned anhydrous carboxylic acids, and furthermoreC₁-C₄-alkanols, for example methanol, ethanol or isopropanol, dialkylethers, cyclic ethers and mixtures of the abovementioned solvents. Forthe oxidative cyclization of substituted thioureas to benzothiazolessee, for example, Houben-Weyl: “Methoden der organischen Chemie” V, Vol.E8B, 1994, p.865 f.

The substituted 2-aminobenzothiazole-5-carboxylic acid of the formulaIV-1a can either be reacted directly in the abovementioned manner with acyclohexane-1,3-dione of the formula III or an activated derivativethereof to give the compound I according to the invention (where Y=S andX=C—NH—R′″, where R″ is C₁-C₆-alkyl or unsubstituted or substitutedphenyl).

If R³ in the formula IV-1a is NH—CH₃, it is also possible to prepare theo-aminothiobenzoic acids of the formula VIII (where R═R′=H) byhydrolysis according to step e). The hydrolysis is generally followed bythe methylation to give the methyl thioether VIII (R=H, R′=CH₃). Thehydrolysis in step e) is carried out, for example, by reacting thecompound IV-1a (where R³=NH—CH₃) with an alkali metal hydroxide, forexample lithium hydroxide, sodium hydroxide or potassium hydroxide, analkaline earthmetal hydroxide or an alkali metal iodide, such as sodiumiodide, in a suitable solvent at elevated temperature, the reactionpreferably being carried out in the absence of oxygen. Customaryreaction temperatures are in the range from 0 to 200° C., in particularin the range from 20 to 180° C. Suitable solvents are, in addition tothe abovementioned aliphatic or cycloaliphatic hydrocarbons, thehalogenated hydrocarbons, the aromatic hydrocarbons, the abovementionedethers and alcohols, in particular aqueous monophasic systems andpyridine. For the hydrolysis of the substituted2-aminobenzothiazole-5-carboxylic acids see, for example: Organikum,16th edition 1986, p. 415; Mc Murry, Org. React. 24 (1976), 187;Taschner et al., Rocz. Chem. 30 (1956), 323; Houben-Weyl: “Methoden derorganischen Chemie”, Volume E8b, 1994, p. 1010 f.; J. Chem. Soc. PerkinTrans., Part 1, No. 12, (1976), 1291-1296, in particular A. R. Katritzkyet al., J. Heterocycl. Chem. 30 (1) (1993), 135-139. The conversion intothe methyl thioether VIII where R=H and R′=CH₃ is carried out in asimple manner by reacting with methyl iodide or dimethyl sulfate.

In a similar manner, it is possible to obtain compounds of the formulaVIII where R=H by initially esterifying the 3-aminobenzoic acid of theformula Xa with a C₁-C₄-alkanol, for example with methanol, in a knownmanner. The resulting ester of the formula Xb (R=C₁-C₄-alkyl, inparticular methyl) is then, in step f), reacted with isothiocyanic acidor a suitable salt of isothiocyanic acid, for example sodiumisothiocyanate, in the presence of a concentrated mineral acid, to givethe thiourea derivative. The reaction conditions correspond to thereaction conditions mentioned under step d) for the urea derivatives.The thiourea derivative is subsequently, in step g), cyclized under theabovementioned conditions to give the 2-aminobenzothiazole-5-carboxylicester of the formula IV-1b (R³=NH₂). The resulting compound of theformula IV-1b where R³=NH₂ can be hydrolyzed in step et to give thecompound VIII, which is subsequently, if appropriate, methylated (VIII:R=H, R′=CH₃).

It is also possible to convert the compound IV-1b in the mannerdescribed above into the compound I according to the invention (whereX=C-NH₂ and Y=S). Moreover, it is possible to initially diazotize the2-amino group of the compound IV-1b and to introduce furtherfunctionalities into the 2-position of the benzothiazole skeleton inthis way. The conversion of R³=NH₂ into R³=halogen is carried out in aknown manner under Sandmeyer conditions. The conversion of R³=NH₂ intoR³=H is carried out in a known manner by successive reaction of the2-aminobenzothiazole-5-carboxylic ester with nitrite under acidconditions and then with a reducing agent, such as hypophosphoric acid,sodium borohydride, trialkylsilanes, trialkylstannanes, SnCl₂, NO,Wilkinson catalysts; see also J. Am. Chem. Soc. 71 (1949), p. 2137; J.Am. Chem. Soc. 72 (1950), p. 3013; 76 (1954), p. 290.

A further route to the compounds of the formula VIII is shown in scheme2.

Starting from 2,4-dicyanothioanisoles of the formula XI, in step h) theamide of the formula XII is prepared by selective hydrolysis. Owing tothe different reactivity of the two methyl groups, the preparation iscarried out under customary alkaline hydrolysis conditions, but theprogress of the reaction is preferably monitored. Methods for thealkaline hydrolysis of nitriles are known, for example, from Org. Synth.Coll. Vol. 1, 1941, p. 321. In a further step i), the amide function inthe compounds of the formula XII is then converted into an aminofunction by Hofmann degradation. This gives compounds of the formulaVIII where R=H and R′=CH₃. Typical conditions for the Hofmanndegradation are: aqueous alkaline chlorine or hypochloride solutions,temperatures in the range from 0 to 150° C., preferably in the rangefrom 20 to 120° C. (see also Organikum, 16th edition 1986, p. 572).

A further route to benzothiazole-5-carboxylic acids is shown in scheme3. This route utilizes the conversion of benzothiazoles of the formulaXIV into the corresponding carboxylic acids, as shown in reaction stepo).

The conversion of the bromobenzothiazole of the formula XIV into thecarboxylic acid of the formula IV-1 (R=H) is carried out, for example,by successive reaction of XIV with magnesium to give the correspondingGrignard compound and subsequent reaction of the Grignard compound withcarbon dioxide. Alternatively, the compound XIV can be converted intothe compound IV-1 by halogen-metal exchange using an alkali metal alkyl,for example a lithium alkyl, such as methyllithium, n-butyllithium ortert-butyllithium, and subsequent reaction of the reaction product withCO₂.

Reaction step o) in scheme 3 can also be realized by reacting the5-bromobenzothiazole of the formula XIV with carbon monoxide, a base andwater, under elevated pressure in the presence of a Pd, Ni, Co or Rhcatalyst.

The catalysts nickel, cobalt, rhodium and in particular palladium can bepresent in metallic form or in the form of customary salts, such as inthe form of halogen compounds, for example PdCl₂, RhCl₃.H₂O, acetates,for example Pd(OAc)₂, cyanides,- etc., in the known valence states.Metal complexes with tertiary phosphines, metal alkylcarbonyls, metalcarbonyls, e.g. CO₂(CO)₈, Ni(CO)₄, metal carbonyl complexes withtertiary phosphines, e.g. (PPh₃)₂Ni(CO)₂, or transition metal saltscomplexed with tertiary phosphines can also be present. Thelast-mentioned embodiment is preferred, in particular when the catalystused is palladium. Here, the type of phosphine ligands is widelyvariable. They can be represented, for example, by the followingformulae:

where n is the number 1, 2, 3 or 4 and the radicals R²⁴ to R²⁶ arelow-molecular-weight alkyl, for example C₁-C₆-alkyl, aryl,C₁-C₄-alkylaryl, for example benzyl or phenethyl, or aryloxy. Aryl is,for example, naphthyl, anthryl and preferably unsubstituted orsubstituted phenyl, where, with respect to the substituents, attentionhas to be paid only to their inertness to the carboxylation reaction,otherwise they can be widely varied and include all inert organocarbonradicals, such as C₁-C₆-alkyl radicals, for examplemethyl, carboxylradicals, such as COOH, COOM (M is, for example, an alkali metal,alkaline earth metal or ammonium salt), ororganocarbon radicals attachedvia oxygen, such as C₁-C₆-alkoxy radicals.

The phosphine complexes can be prepared in a manner known per se, forexample as described in the documents mentioned at the outset. Forexample, customary commercially available metal salts such as PdCl₂ orPd(OCOCH₃)₂ are used as starting materials and the phosphine, forexample P(C₆H₅)₃, P(n—C₄H₉)₃, PCH₃(C₆H₅)₂,1,2-bis(diphenylphosphino)ethane, is added.

The amount of phosphine, based on the transition metal, is usually from0 to 20, in particular from 0.1 to 10, molar equivalents, particularlypreferably.from 1 to 5 molar equivalents.

The amount of transition metal is not critical. Of course, for reasonsof cost, preference is given to using a small amount, for example from0.1 to 10 mol%, in particular from 1 to 5 mol%, based on the startingmaterial IV.

For preparing the benzothiazole-5-carboxylic acids IV-1 (R═OH), thereaction is carried out with carbon monoxide and at least equimolaramounts of water, based on the starting materials XIV. The reactioncomponent water can simultaneously also serve as solvent, i.e. themaximum amount is not critical.

However, depending on the nature of the starting materials and thecatalysts used, it may also be advantageous for the solvent used to be,instead of the reaction component, another inert solvent or the basewhich is used for the carboxylation.

Suitable inert solvents for carboxylation reactions are customarysolvents such as hydrocarbons, for example toluene, xylene, hexane,pentane, cyclohexane, ethers, for example methyl tert-butyl ether,tetrahydrofuran, dioxane, dimethoxyethane, substituted amides, such asdimethylformamide, persubstituted ureas, such as tetra-C₁-C₄-alkylureas,or nitriles, such as benzonitrile or acetonitrile.

In a preferred embodiment of the process, one of the reactioncomponents, in particular the base, is used in an excess, so that noadditional solvent is necessary

Bases which are suitable for the process are all inert bases which areable to bin d hydrogen iodide or hydrogen bromide liberated during thereaction. Examples which may be mentioned here are tertiary amines, suchas tert-alkylamines, for example trialkylamines, such as triethylamine,cyclic amines, such as N-methylpiperidine or N,N′-dimethylpiperazine,pyridine, alkali metal carbonates or bicarbonates, ortetraalkyl-substituted urea derivatives, such as tetra-C₁-C₄-alkylurea,for example tetramethylurea,

The amount of base is not critical, customarily from 1 to 10, inparticular from 1 to 5, mol are used when the base is simultaneouslyused as solvent, the amount is generally such that the fractioncomponents are dissolved, unnecessarily high excesses being avoided forreasons of practicability in order to save costs, to be able to employsmall reaction vessels and to ensure that the reaction components havemaximum contact.

During the reaction, the carbon monoxide pressure is adjusted such thatan excess of Co, based on XIV, is always present. At room temperature,the carbon monoxide pressure is preferably from 1 to 250 bar, inparticular from 5 to 150 bar, of CO.

The carbonylation is generally carried out continuously o r batchwise atfrom 20 to 250° C., in particular from 30 to 150° C. In the case ofbatchwise operation, carbon monoxide is advantageously continuouslyinjected onto the reaction mixture to maintain a constant pressure.

The 5-bromobenzothiazoles XIV used as starting materials are known orcan easily be prepared by suitable combination of known syntheses andaccording to the reaction sequence described in scheme 3.

According to scheme 3, it is possible, for example, to converto-chloronitrobenzenes of the formula XIII into the correspondingo-nitrothioethers using alkali metal salts of alkylmercaptans (step k).The resulting thioether can be brominated selectively in the 3-positionwith respect to the nitro group (step 1). Brominating reagents which arecustomarily used for this purpose are, in addition to bromine—ifappropriate in combination with a Lewis acid such as FeBr₃ —, alsoN-bromosuccinimide, N-bromohydantoin and pyridinium perbromide. Thebromination is preferably carried out in an organic solvent, for examplean aliphatic or cycloaliphatic hydrocarbon, halogenated hydrocarbon oranhydrous organic acids, at temperatures in the range from −15 to 150°C., preferably in the range from −15 to 100° C. (see, for example,organikum, 16th edition, 1986, p. 315). Subsequently, in step m), thenitro group is reduced to the amino group. The conditions for step m)correspond to the conditions given for step c) in scheme 1. Theo-aminothioether from step m) is subsequently, in step n), cyclized tothe 5-bromobenzothiazole XIV. The reaction conditions required for thisstep correspond to the conditions given for step a) in scheme 1.

For preparing the benzothiazole S-dioxide compounds of the formula I(Y=SO₂), for example, the benzothiazole-5-carboxylic acids IV-1a orIV-1b or the 5-bromobenzothiazole-5-carboxylic acids XIV are reactedwith an oxidizing agent giving the corresponding S-dioxide, which isthen processed further as described to give the target compound of theformula I where Y=SO₂. However, preference is given to initiallyoxidizing the thiomethyl ether of the formula VIII (scheme 1, formulaVIII where R=H and R′=CH₃) to give the S-dioxide VIIIc, which issubsequently cyclized to give the benzothiazole S-dioxide 5-carboxylicacid of the formula IV-1c.

The oxidation of VIII to the S-dioxide is carried out using oxidizingagents, such as peroxy acids, for example m-chloroperbenzoic acid,peroxyacetic acid, trifluoroperoxyacetic acid, or using hydrogenperoxide, which is preferably employed together with a transition metalcatalyst, for example sodium tungstate (VI). The cyclization ofo-methylsulfonylaminobenzenes of the formula VIIIc is carried outanalogously to the method described in Chem. Heterocycl. Comp. Vol.3,1967, p.197 ff.

A synthesis of benzoxazole-5-carboxylic acid derivatives of the formulaIV-2 (X=C—R³, Y═O) is described in scheme 4. Here, starting from3-nitrotoluenes of the formula IX, a 3-aminobenzoic. ester of theformula Xb (R=C₁-C₄-alkyl) is initially prepared in the manner describedfor scheme 1. In step p), the amino group in Xb is first diazotized in aknown manner, and the product is subsequently reacted with alkali metalazides to give the corresponding 3-azidobenzoic acids of the formula XV.The azide XV is then, in reaction step q), reacted with analkanecarboxylic acid, which may also be halogenated, for example formicacid, acetic acid, trifluoroacetic acid or propionic acid, to give thebenzoxazole-5-carboxylic ester of the formula IV-2a (R³=C₁-C₄-alkyl).The compound IV-2a can either be reacted directly to give thecyclohexenone derivative of the formula I according to the inventionwhere X=CR³ and Y═O or, alternatively, be hydrolyzed in reaction step r)to give the o-aminophenol of the formula XVI. Like theo-aminothiophenols of the formula VIII, the compounds XVI can then beconverted into the benzoxazole-5-carboxylic esters of the formula IV-2.

In reaction step p), initially an aromatic diazonium compound isprepared from the amine of the formula Xb, in aqueous acidic solution orin an anhydrous acid, such as formic acid, acetic acid ortrifluoroacetic acid, using an inorganic nitrite, such as sodiumnitrite, or an organic nitrite, such as isoamyl nitrite. An alkali metalazide, for example sodium azide, is then added to the solution orsuspension of the diazonium compound, giving the 3-azidobenzoic esteraccording to scheme 4. The reaction temperature for the reaction isgenerally in the range from −15 to +50° C., preferably in the range from0 to 20° C. See also K. G. Pinney et al., J. Org. Chem. [JOCEAH] 56 (9)(1991), 3125-3133.

Reaction step q) is preferably carried out in the anhydrous acid HOOC—R³which is desired for the condensation, in an aromatic hydrocarbon, suchas benzene, toluene, xylene or chlorobenzene. The reaction temperatureis generally in the range from 0 to 150° C. and preferably in the rangefrom 50 to 145° C. (See also B. Decroix et al., Bull. Soc. Chim. Fr.1976, 621; S. Chaudhury et al., Can. J. Chem. 60 (1982), 1122). Thehydrolysis of the benzoxazole-5-carboxylic ester obtained in step q) togive the 3-amino-4-hydroxybenzoic ester of the formula XVI is carriedout, for example, under the conditions given for reaction step e) inscheme 1. The condensation of compound XVI to thebenzoxazole-5-carboxylic ester in step s) is carried out, for example,under the reaction conditions given for step a) in scheme 1. (For steps), see also Houben-Weyl, “Methoden der organischen Chemie”, Vol. E8a,1993, p. 1020 f.)

Another route to the benzoxazole-5-carboxylic acids of the formula IV(X=C—R³, Y═O) is shown in scheme 5.

Here, an o-chloronitrobenzene of the formula XIII is initially convertedby nucleophulic exchange of halogen for methoxy into an o-nitroanisole(step t)). This is then brominated under the reaction conditions givenfor step 1) in scheme 3, the bromine atom being introduced selectivelyinto the p position to the methoxy group. The brominated nitroanisole isthen initially reduced selectively to give the amino compound, and thehydroxyl function is subsequently released by ether cleavage. This gives2-amino-4-bromophenols. These are then cyclized to the5-bromobenzoxazole of the formula XVII under the reaction conditionsgiven for step s). The compound XVII is then reacted under the reactionconditions described for step o) in scheme 3 to give thebenzoxazole-5-carboyxlic acid of the formula IV (X=C—R³ and Y═O).

A process for preparing benzimidazole-5-carboxylic esters is shown inscheme 6.

Once more, 3-nitrotoluenes are used as starting materials here, X andthey are converted in the manner described above into 3-aminobenzoicesters of the formula Xb. The compounds Xb are then, in reaction stepy), reacted with a carboxylic acid of the formula R³-CO₂H or a reactivecarboxylic acid equivalent RCOL¹, where L¹ is as defined above, to givea carboxamide of the formula XVIII. Here, R³ has one of the meaningsgiven above. XVIII is then converted under acidic conditions, forexample with phosgene or phosphoryl chloride, into a nitrilium ion,which is quenched with an amine of the formula R⁴-NH₂ or ammonia,resulting in an imino amide of the formula XIX. The compound XIX canthen be converted under oxidizing conditions, as described, for example,for reaction step b) or g) in scheme 1, into thebenzimidazole-5-carboxylic ester, which for its part can be hydrolyzedto give the carboxylic acid.

Step y) is generally carried out under the customary reaction conditionsfor forming carboxamides from carboxylic acids or carboxylic acidderivatives and aromatic amines. The reaction temperature is generallyin the range from −15 to 200° C., preferably in the range from 20 to150° C.

For preparing the imino amide of the formula XIX, the amide of theformula XVIII is initially dissolved under exclusion of water in anorganic solvent, for example one of the abovementioned cycloaliphatic oraromatic hydrocarbons or an ether, and converted into the nitrilium ionusing an inorganic acid, for example hydrochloric acid or sulfuric acid,a Lewis acid, such as titanium tetrachloride, or an acid chloride, suchas sulfonyl chloride, sulfuryl chloride, phosphoryl chloride orphosgene. The required temperatures for this are generally in the rangefrom −15 to 150° C. and preferably in the range from 20 to 140° C. Thenitrilium ion is then quenched with ammonia or an amine of the formulaR⁴-NH_(2.)

The cyclization of the compound XIX to the benzimidazole-5-carboxylicester of the formula IV (X=C—R³, Y=C—R⁴) is generally carried out usingan oxidizing agent, such as lead tetraacetate, thallium(III)nitrite,sulfuryl chloride or sodium hypochloride, under anhydrous conditions.Suitable solvents are, for example, aliphatic or cycloaliphatichydrocarbons, aromatic hydrocarbons or ethers. The reaction is generallycarried out in the range from −15 to +150° C. and preferably in therange from 0 to 140° C. For the preparation of benzimidazoles fromiminoamides see also Can. J. Chem. 60 (1982), p.1122.

Benzoisothiodiazoles of the formula IV-4 (X—Y=S═N) are prepared, forexample, starting from benzimidazole-5-carboxylic acids or their esters,in the manner described in scheme 7.

In this case a benzimidazolecarboxylic ester or the free, carboxylicacid is initially hydrolyzed to 3,4-diaminobenzoic acid. This issubsequently cyclized with sulfurous acid or its derivatives, forexample SO₂ or SO₂Cl₂, to give the benzoisothiadiazole-5-carbbxylic acidof the formula IV-4. The cyclization is usually carried out at from 0 to200° C. and preferably in the range from 50 to 150° C., for example in asolvent or in the melt (see also: Chem. Ber. 100 (1967), p. 2164).

Benzothiadiazole-5-carboxylic acids of the formula IV-5 (X=N, Y=S) canbe prepared starting from 2-aminothiophenol-5-carboxylic acids of theformula VIII (R=R′=H). To this end, the compounds of the formula VIIIare initially diazotized, for example by reaction with organic orinorganic nitrite in an aqueous neutral reaction medium in the rangefrom −15 to +20° C. The aqueous solution or suspension of the diazoniumsalt is subsequently acidified, whereupon the compound of the formulaIV-5 forms. This can be obtained in a conventional manner from thereaction mixture, for example by extraction with an organic solvent. Thepreparation of the starting materials VIII is described in scheme 1. Thebenzothiadiazolecarboxylic acids IV-5 (X=N, Y=S) can be prepared, forexample, analogously to the process described in U.S. Pat. No.5,770,758.

EXAMPLES

Abbreviations used:

EDC=ethyl(3′-dimethylaminopropyl)carbodiimide

DMAP=4-dimethylaminopyridine

5-(1′-Hydroxycyclohex-2′-en-3′-on-2′-ylcarbonyl)-1-methylbenzo-triazole(Example 1)

1.1 Cyclohexen-3-on-1-yl 1-methylbenzotriazole-5-carboxylate

1.5 g of 1-methylbenzotriazole-5-carboxylic acid (8.5 mmol) and 1.0g of1,3-cyclohexanedione (8.9 mmol) were dissolved in 30 ml of abs.acetonitrile and admixed with 1.6 g of EDC (8.5 mmol), 2 ml oftriethylamine and a cat. amount of DMAP. After the reaction had ended,the solution was poured into water and extracted with ethyl acetate. Theorganic phase was washed and dried and the product was then purified bycrystallization. Yield: 1.35 g (59%).

m.p.: 154-158° C.

1.25-(1′-Hydroxycyclohex-2′-en-3′-on-2′-ylcarbonyl)-1-methylbenzotriazole

0.74 g (2.7 mmol) of cyclohexen-3-on-1-yl1-methylbenzotriazole-5-carboxylate was dissolved in 30 ml ofacetonitrile and admixed with 0.53 g of triethylamine (5.3 mmol) and0.15 g of trimethylsilyl cyanide (1.5 mmol). The mixture was stirred atroom temperature until the reaction had gone to completion, the solventwas removed under reduced pressure and the residue was taken up inwater. The aqueous phase was extracted with methylene chloride, adjustedto pH 2 and extracted with ethyl acetate. The solvent was removed andthe product was then purified by trituration. Yield: 0.5 g (68%).

¹H NMR (D₆-DMSO, TMS) δ=2.03 (m, 2H); 2.48 (m, 4H); 4.37 (s,3H); 7.90(d, 1H); 7.98 (d, 1H); 8.22 (s, 1H).

The compounds of Example 2 to 40 were prepared analogously by reactingthe respective carboxylic acid IVa with the appropriatecycolhexan-1,3-dione.

Ex. Structure/Compound No. M.p. [° C.] or ¹H-NMR [ppm]  1

D₆-DMSO, TMS: 2.03(m, 2H), 2.48(m, 4H), 4.37(s, 3H), 7.90(d, 1H),7.98(d, 1H), 8.22(s, 1H) ppm.  2

211-215° C.  3

127-130° C.  4

CDCl₃, TMS: 1.12(s, 6H), 2.34(s, 2H), 2.59(s, 3H), 2.65(s, 2H), 7.18(d,1H), 7.63(d, 1H), 17.64(OH) ppm.  5

CDCl₃, TMS: 1.12(s, 6H), 2.35(s, 2H), 2.64(s, 2H), 2.70(s, 2H),7.1-7.2(m, 3H), 7.76(d, 1H), 8.05-8.15(m, 2H), 17.75(OH) ppm.  6

CDCl₃, TMS: 1.13(s, 6H), 2.35(s, 2H), 2.64(s, 2H), 2.72(s, 2H), 3.87(s,3H), 6.98(d, 2H), 7.1(d, 1H), 7.73(d, 1H), 8.02(d, 2H), 17.78(OH) ppm. 7

CDCl₃, TMS: 2.04(m, 2H), 2.45(t, 2H), 2.74(s, 3H), 2.79(t, 2H), 3.84(s,3H), 6.98(d, 2H), 7.1(d, 1H), 7.72(d, 1H), 8.02(d, 2H), 17.68(OH) ppm. 8

120-122° C.  9

154-155° C. 10

148-150° C. 11

158-160° C. 12

150-155° C. 13

CDCl₃, TMS: 1.42(t, 3H), 2.04(m, 2H), 2.55(s, 3H), 2.63(4H), 2.98(q,2H), 7.07(d, 1H), 7.33(d, 1H), 17.64(OH) ppm. 14

CDCl₃, TMS: 1.42(t, 3H), 1.7-1.85(m, 2H), 2.0-2.34(m, 4H), 2.48(s, 3H),2.9(1H), 2.98(q, 2H), 3.18(1H), 7.08(d, 1H), 7.33(d, 1H), 17.68(OH) ppm.15

112-115° C. 16

CDCl₃, TMS: 1.34(s, 6H), 1.49(s, 9H), 1.56(s, 6H), 2.70(s, 3H), 7.04(d,1H), 7.7(d, 1H), 17.95(OH) ppm. 17

CDCl₃, TMS: 1.42(d, 6H), 2.08(m, 2H), 2.46(2H), 2.64(s, 3H), 2.8(2H),3.42(m, 1H), 7.09(d, 1H), 7.7(d, 1H), 17.7(OH) ppm. 18

CDCl₃, TMS: 1.7-1.85(m, 2H), 2.0-2.34(m, 4H), 2.48(s, 3H), 2.9(1H),3.18(1H), 3.92(s, 3H), 7.0-7.1(m, 3H), 7.25-7.38(m, 2H), 7.67(d, 1H),17.65(OH) ppm. 19

138-141° C. 20

CDCl₃, TMS: 2.04(m, 2H), 2.42(2H), 2.46(s, 3H), 2.77(2H), 7.02(d, 1H),7.15-7.33(m, 3H), 7.4-7.55(m, 2H), 17.63(OH) ppm. 21

CDCl₃, TMS: 1.14(s, 6H), 1.42(t, 3H), 2.36(s, 2H), 2.54(s, 3H), 2.69(s,2H), 2.98(q, 2H), 7.08(d, 1H), 7.3(d, 1H), 17.7(OH) ppm. 22

CDCl₃, TMS: 1.7-1.85(m, 2H), 2.0-2.34(m, 4H), 2.63(s, 3H), 2.9(1H),3.18(1H), 7.08(d, 1H), 7.15-7.33(m, 3H), 7.6(dd, 1H), 7.7(d, 1H),17.6(OH) ppm. 23

122-174° C. 24

 92-98° C. 25

 97-101° C. 26

160-167° C. 27

 99-101° C. 28

167-170° C. 29

127-143° C. 30

128-136° C. 31

CDCl₃, TMS: 1.42(t, 3H), 1.7-1.9(m, 2H), 2.0-2.3(m, 4H), 2.62(s, 3H),2.9(1H), 3.18(m, 3H), 7.1(d, 1H), 7.7(d, 1H), 17.7(OH) ppm. 32

CDCl₃, TMS: 1.7-1.8(m, 2H), 2.0-2.3(m, 4H), 2.6(s, 3H), 2.78(s, 3H),2.9(1H), 3.18(1H), 7.04(d, 1H), 7.58(d, 1H), 17.7(OH) ppm. 33

 70-73° C. 34

149-152° C. 35

CDCl₃, TMS: 2.0(m, 2H), 2.52(2H), 2.59(s, 3H), 2.78(s, 3H), 2.9(2H),7.03(d, 1H), 7.6(d, 1H), 17.7(OH) ppm. 36

CDCl₃, TMS: 1.3(s, 6H), 1.38(s, 6H), 2.78(s, 3H), 7.27(d, 1H), 7.88(d,1H), 17.7(OH) ppm. 37

129-133° C. 38

125-128° C. 39

CDCl₃, TMS: 1.7-1.85(m, 2H), 2.0-2.34(m, 4H), 2.62(s, 3H), 2.9(1H),3.18(1H), 4.93(s, 2H), 7.17(d, 1H), 7.77(d, 1H), 17.7(OH) ppm. 40

 95-97° C.

The compounds of the formula I and their agriculturally useful salts aresuitable, both as isomer mixtures and in the form of the pure isomers,for use as herbicides. The herbicidal compositions comprising compoundsof the formula I effect very good control of vegetation on non-cropareas, especially at high application rates. In crops such as wheat,rice, maize, soybeans and cotton, they act against broad-leaved weedsand grass weeds without causing any significant damage to the cropplants. This effect is observed in particular at low application rates.

Depending on the application method in question, the compounds of theformula I or the herbicidal compositions comprising them canadditionally be employed in a further number of crop.plants foreliminating undesirable plants. Suitable crops are, for example, thefollowing:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I can also be used in cropswhich tolerate the action of herbicides due to breeding, includinggenetic engineering methods.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be applied, for example, in the form of directlysprayable aqueous solutions, powders, suspensions, includinghighly-concentrated aqueous, oily or other suspensions or dispersions,emulsions, oil dispersions, pastes, dusts, materials for broadcasting orgranules, by means of spraying, atomizing, dusting, broadcasting orpouring. The use forms depend on the intended purposes; in each case,they should ensure the finest possible distribution of the activeingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I and usually the auxiliaries which are customarily used forformulating crop protection agents.

Suitable inert auxiliaries are essentially:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffin, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexenone, strongly polar solvents, for example amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions,thebenzoheterocyclylcyclohexenones of the formula I, as such or dissolvedin an oil or solvent, can be homogenized in water by means of wettingagent, tackifier, dispersant or emulsifier. Alternatively, it ispossible to prepare concentrates of active substance, wetting agent,tackifier, dispersant or emulsifier and, if desired, solvent or oil, andthese concentrates are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, for example ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fattyacids, of alkyl- and alkylarylsulfonates, of alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and the salts of sulfatedhexa-, hepta- and octadecanols and of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, con densates of naphthalene or of the naphthalenesulf onicacids with phenol and formaldehyde, polyoxyethylene octyxphenol ether,ethoxyoated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycolether, tributylphenyl polyglycol ether, alkylaryl polyester alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixingor concomitant grinding of the active substances with a solid carrier.

Granules , e.g. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Solid carriers are mineral earths such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk , bole, less,clay, dolomite, diatomacetus earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, aiionium phosphate, ammonium nitrate, ureas, andproducts of vegetable origin such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-useproducts can be varied within wide ranges. In general, the formulationscomprise approximately from 0.001 to 98% by weight, preferably 0.01 to95% by weight, of at least one active ingredient. The active ingredientsare employed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The formulation examples which follow illustrate the preparation of suchproducts:

I. 20 parts by weight of the compound of the formula I in question aredissolved in a mixture composed of 80 parts by weight of alkylatedbenzene, 10 parts by weight of the adduct of 8 to 10 mol of ethyleneoxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight ofcalcium dodecylbendzenesulfonate and 5 parts by weight of the adduct of40 mol of ethylene oxide to 1mol of castor oil. Pouring the solutioninto 100,000 parts by weight of water and finely distributing it thereingives an aqueous dispersion which comprises 0.02% by weight of theactive ingredient.

II. 20 parts by weight of the compound of the formula I in question aredissolved in a mixture composed of 40 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weightof the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.Pouring the solution into 100,000 parts by weight of water and finelydistributing it therein gives an aqueous dispersion which comprises0.02% by weight of the active ingredient.

III. 20 parts by weight of the compound of the formula I in question aredissolved in a mixture composed of 25 parts by weight of cyclohexanone,65 parts by weight of a mineral oil fraction of boiling point 210 to280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxideto 1 mol of castor oil. Pouring the solution into 100,000 parts byweight of water and finely distributing it therein gives an aqueousdispersion which comprises 0.02% by weight of the active ingredient.

IV. 20 parts by weight of the compound of the formula I in question aremixed thoroughly with 3 parts by weight of sodiumdiisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt ofa lignosulfonic acid from a sulfite waste liquor and 60 parts by weightof pulverulent silica gel, and the mixture is ground in a hammer mill.Finely distributing the mixture in 20,000 parts by weight of water givesa spray mixture which comprises 0.1% by weight of the active ingredient.

V. 3 parts by weight of the compound of the formula I in question aremixed with 97 parts by weight of finely divided kaolin. This gives adust which comprises 3% by weight of the active ingredient.

VI. 20 parts by weight of the compound of the formula I in question aremixed intimately with 2 parts by weight of calciumdodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglylcolether, 2 parts by weight of the sodium salt of aphenol/urea/formaldehyde condensate and 68 parts by weight of aparaffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound of the formula I in question isdissolved in a mixture composed of 70 parts by weight of cyclohexanone,20 parts by weight of ethoxylated isooctylphenol and 10 parts by weightof ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound of the formula I in question isdissolved in a mixture composed of 80 parts by weight of cyclohexanoneand 20 parts by weight of Wettol^(R)EM 31 (=non-ionic emulsifier basedon ethoxylated castor oil). This gives a stable emulsion concentrate.

The compounds of the formula I, or the herbicidal compositions, can beapplied pre- or post-emergence. If the active ingredients are less welltolerated by certain crop plants, it is possible to use applicationtechniques in which the herbicidal compositions are sprayed, with theaid of the spraying equipment, in such a way that they come into aslittle contact as possible,if any, with the leaves of the sensitive cropplants while the active ingredients reach the leaves of undesirableplants which grow underneath, or the bare soil surface (post-directed,lay-by).

Depending on the control target, the season, the target plants and thegrowth stage, the rates of application of the compound of the formula Iare from 0.001 to 3.0, preferably 0.01 to 1.0, kg of active substance(a.s.)/ha.

To widen the spectrum of action and to achieve synergistic effects, thecompounds of the formula I according to the invention may be mixed, andapplied jointly, with a large number of representatives of other groupsof herbicidal or growth-regulating active ingredients. Suitable examplesof components in mixtures are 1,2,4-thiadiazoles, 1,3,4-thiadiazoles,amides, aminophosphoric acid and its derivatives, aminotriazoles,anilides, aryloxy/hetaryloxyalkanoic acids and their derivatives,benzoic acid and its derivatives, benzothiadiazinones,2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-p henycpropionic acidand its derivatives, pyrazole, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones,etriazolinones,triazolecarboxamides and uracils.

Moreover, it may be advantageous to apply the compounds of the formulaI, alone or in combination with other herbicides, even in the form of amixture together with further crop protection agents, for example withpesticides or agents for controlling phytopathogenic fungi or bacteria.Also of interest is the miscibility with mineral salt solutions whichare employed for treating nutritional and trace element deficiencies.

USE EXAMPLES

The herbicidal activity of the compounds of the formula I according tothe invention was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, suspended oremulsified in water, were applied directly after sowing by means offinely distributing nozzles. The containers were irrigated gently topromote germination and growth and subsequently covered with translucentplastic hoods until the plants had rooted. This cover caused uniformgermination of the, test plants unless this was adversely affected bythe active ingredients.

For the post-emergence treatment, the test plants were first, grown to aplant height of from 3 to 15 cm, depending on the plant habit, and onlythen treated with the active ingredients which had been suspended oremulsified in water. To this end, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment. The rat e of application for the post-emergencetreatment was 0.25 or 0.125 kg of a.s. (active substance)/ha.

Depending on the species, the plants were kept at from 10 to 25° C., or20 to 35° C., respectively. The test period extended over 2 to 4 weeks.During this time, the plants were tended, and their response to theindividual treatments was evaluated.

Evaluation was carried out using a scale of from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies:

Bayer-code Common name AMARE redroot pigweed AVEFA wild oats CHEALlambsquarters (goosefoot) CAPBP shepherd's purse DIGSA fingergrass,hairy ECHCG barnyard grass EPHHL spurge GASPA smallflower GALAPcatchweed bedstraw LAMAM henbit MYOAR forget-me-not PAPRH corn poppyPOLPE ladysthumb SETIT foxtail STEME common chickweed SOLNI blacknightshade THLAR fanweed TRZAS spring wheat PHBPU tall morninggloryABUTH velvet leaf SETFA giant foxtail

The following experiments were performed by the post-emergence method.

At application rates of 0.25 and 0.5 kg/ha (a.s.), the compound I-1a.394of example 2 showed very good herbicidal action against the harmfulplants AMARE, CHEAL, IPOSS and POLPE, and selectivity in wheat, whenapplied by the post-emergence method.

At application rates of 0.25 and 0.5 kg/ha (a.s.), the compound I-1c.396of example 4 shows good to very good herbicidal action against AMARE,CHEAL, ECHCG and SETFA, when applied by the post-emergence method.

At application rates of 0.125 and 0.25 kg/ha (a.s.), the compoundI-2a.406 of example 13 shows very good herbicidal action againstABUTH,AMARE, CHEAL and IPOSS and a good herbicidal action against GALAP,when applied by the post-emergence method.

At application rates of 0.0625 and 0.125 kg/ha (a.s.),the compoundI-2x.406 of example 14 shows good to very good herbicidal action againstABUTH, CHEAL, ECHCG and POLPE, when applied by the post-emergencemethod.

At application rates of 0.25 and 0.125 kg/ha (a.s.), the compoundI-1a.405 of example 13 shows very good herbicidal action against AMARE,CHEAL, ECHCG and POLPE, when applied by the post-emergence method.

At application rates of 0.125 and 0.25 kg/ha (a.s.), the compoundI-1a.408 of example 17 shows good to very good herbicidal action againstABUTH, CHEAL, ECHCG and POLPE, when applied by the post-emergencemethod.

At application rates of 0.125 and 0.25 kg/ha (a.s.), the compoundI-1x.790 of example 22 shows very good herbicidal action against CHEAL,ECHCG, POLPE and SETFA when applied by the post-emergence method.

At application rates of 0.125 and 0.25 kg/ha (a.s.), the compoundI-1x.420 of example 24 shows very good herbicidal action against CHEAL,ECHCG, PHPBU, SETFA and POLPE when applied by the post-emergence method.

At application rates of 0.125 and 0.25 kg/ha (a.s.), the compoundI-1x.406 of example 31 shows very good herbicidal action against ABUTH,CHEAL, ECHCG and POLPE when applied by the post-emergence method.

At application rates of 0.0625 and 0.125 kg/ha (a.s.), the compoundI-1x.435 of example 32 shows very good herbicidal action against AMARE,CHEAL and ECHCG when applied by the post-emergence method.

We claim:
 1. A cyclohexenone compound of benzo-fused unsaturated5-membered nitrogen heterocycles of the formula I,

in which X is a group C—R³ or N; Y is N-R⁴, S, SO, SO₂ R¹ is hydrogen,nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl,C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, ordi(C₁-C₆-alkyl)amino-C₁-C₆-alkyl; R² is hydrogen, halogen orC1-C6-alkyl; R³ is hydrogen, halogen, nitro, cyano, hydroxyl, amino,mercapto, thiocyanato, hydrazide, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-hydroxyalkyl, C₁-C₆-aminoalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-hydroxyalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, isC₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino, where thealkyl and cycloalkyl groups of the three last-mentioned radicals may bepartially or fully halogenated and/or may carry one to threesubstituents selected from the group consisting of C₁-C₄-alkoxy andhydroxyl, is C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-hydroxyalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, is phenyl,naphthyl, phenoxy, phenylamino, diphenylamino, where the phenyl groupsof the five last-mentioned radicals for their part may be partially orfully halogenated and/or may carry one, two or three substituentsselected from the group consisting of nitro, cyano, hydroxyl,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, isC(O)OR⁵, or C(O)N(R⁶)R⁷; and R⁴ is hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, isphenyl, naphthyl, where the two last-mentioned radicals for their partmay be partially or fully halogenated and/or may carry one, two or threesubstituents selected from the group consisting of nitro, cyano,hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; where R⁵ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl is phenyl, or naphthyl,where the two last-mentioned radicals for their part may be partially orfully halogenated and/or may carry one, two or three substituentsselected from the group consisting of nitro, cyano, hydroxyl,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R⁶, R⁷independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, are phenyl or naphthyl,where the two last-mentioned radicals for their part may be partially orfully halogenated and/or may carry one, two or three substituentsselected from the group consisting of nitro, cyano, hydroxyl,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and Hexis substituted (3-oxo-1-cyclohexen-2-yl)carbonyl of the formula IIa

 where the variables R⁸ to R¹⁴ are as defined below: R⁸ is hydroxyl,mercapto, halogen, OR¹⁵, SR¹⁵, SOR¹⁶, SO₂R¹⁶, OSO₂R¹⁶, P(O)R¹⁷R¹⁸,OP(O)R¹⁷R¹⁸, P(S)R¹⁷R¹⁸, OP(S)R¹⁷R¹⁸, NR¹⁹R²⁰, or ONR¹⁹R²⁰ which may bepartially or fully halogenated and/or may carry one, to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R⁹, R¹³ independent of one another arehydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl; R¹⁰, R¹², R¹⁴ independentlyof one another are hydrogen or C₁-C₄-alkyl; R¹¹ is hydrogen, halogen,hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, di(C₁-C₆-alkoxy)methyl, (C₁-C₆-alkoxy) (C₁-C₆-alkylthio)methyl, di(C₁-C₆-alkylthio)methyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl;is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl,1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the sixlast-mentioned radicals may be substituted by one to three C₁-C₄-alkylradicals; or R¹⁰ and R¹² or R¹² and R¹⁴ together form a π bond or aC₁-C₅-alkyl chain which may carry one, two or three radicals from thefollowing group: halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl orC₁-C₄-allkoxycarbonyl; or R¹⁰ and R¹⁴ together form a C₁-C₄-alkyl chainwhich may carry one, two or three radicals from the following group:halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; orR¹¹ and R¹² together form an —O—(CH₂)_(p)—O—, —O—(CH₂)_(p)—S—,—S—(CH₂)_(p)—S—, —O—(CH₂)_(q)— or —S—(CH₂)_(q)— chain in which p is 2,3, 4 or 5 and q is 2, 3, 4, 5 or 6, and which may be sustituted by one,two or three radicals from the following group: halogen, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkocycarbonyl; or R¹¹ and R¹²together with the carbon to which they are attached form a carbonylgroup;  where R¹⁵ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl,C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl,C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl,C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl,C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₁-C₆-alkoxy)-N-(C₁-C₆-alkyl)aminocarbonyl,N-(C₃-C₆-alkenyl)-N-(C1-C6-alkoxy)aminocarbonyl,N-(C₃-C₆-alkynyl)-N-(C₁-C₆-alkoxy)aminocarbonyl,di(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, wherethe alkyl, cycloalkyl and alkoxy radicals mentioned may be partially orfully halogenated and/or may carry one two or three of the followinggroups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl ,C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl; is phenyl,phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl,phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl,N-(C₁-C₆-alkyl)-N-phenylaminocarbonyl, phenyl-C₂-C₆-alkenylcarbonylradical of the 3 last-mentioned substituents may be partially or fullyhalogenated and/or may carry one, to three of the following radicals:nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; R¹⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl orC₃-C₆-cycloalkyl, where the four radicals mentioned may be partially orfully halogenated and/or may carry one, two or three of the followinggroups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl orC₁-C₄-haloalkoxycarbonyl; is phenyl, or phenyl-C₁-C₄-alkyl where thephenyl radical of the two last-mentioned substituents may be partiallyor fully halogenated and/or may carry one, two or three of the followingradicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R¹⁷, R¹⁸ independently of oneanother are hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the threelast-mentioned substituents may be partially or fully halogenated and/ormay carry one, two or three of the following radicals: nitro, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy orC₁-C₄-alkoxycarbonyl; R¹⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl,C₁-C₆-alkylcarbonyl, hydroxyl, C₁-C₆-alkoxy, C₃-C₈-alkenyloxy,C₃-C₆-alkynyloxy, amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino orC₁-C₆-alkylcarbonylamino, where the alkyl, cycloalkyl and alkoxyradicals mentioned may be partially or fully halogenated and/or maycarry one, two or three of the following radicals: cyano,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl,di(C₁-C₄-alkyl)aminocarbonyl or C₃-C₆-cycloalkyl; is phenyl,phenyl-C₁-C₄-alkyl, phenylcarbonyl or where the phenyl radical of thethree last-mentioned substituents may be partially or fully halogenatedand/or may carry one to three of the following radicals: nitro, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R²⁰ ishydrogen, C1-C6-alkyl or C3-C6-alkenyl, C3-C6-alkynyl; and itsagriculturally useful salts.
 2. A pyrazole compound as claimed in claim1 where X in the formula I is C—R³, where R³ is hydrogen, halogen,cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, is phenyl, whichmay be partially or fully halogenated and/or may carry one of thefollowing radicals: C₁-C₄-alkoxy, C₁-C₄-haloalkyl, and C₁-C₄-haloalkoxy;or is COOR⁵ where R⁵ is as defined in claim
 1. 3. A cyclohexenonecompound as claimed in claim 1 wherein Hex in the formula I is a radicalof the formula IIa, where R⁸ is selected from the group consisting ofhydroxyl, mercapto halogen OR¹⁵, SR¹⁵, SO₂R¹⁶, NR¹⁹R²⁰ and ONR¹⁹R²⁰,where R¹⁵, R¹⁶, R¹⁹ and R²⁰ are as defined in claim
 1. 4. Acyclohexenone compound as claimed in claim 3, where in the formula IIaR⁸ is selected from the group consisting of hydroxyl, C₁-C₄-alkyloxy,C₁-C₄-alkylamino, di-C₁-C₄-alkylamino,N-(C₁-C₄-alkoxy)-N-(C₁-C₄-alkyl)amino, O—CH₂-phenyl, phenylthio,phenylcarbonyloxy, 2-, 3- or 4-fluorophenylcarbonyloxy,C₁-C₄-methylthio, C₁-C₄-sulfonyloxy, phenylsulfonyloxy and 2-, 3- or4-methylphenylsulfonyloxy.
 5. A cyclohexenone derivative as claimed inclaim 1, wherein in the formula IIa or IIB R⁹, R¹⁰, R¹¹, R¹², R¹³ andR¹⁴ independently of one another are hydrogen or C₁-C₄-alkyl, R¹¹ mayalso be hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₆ haloalkoxy orC₁-C₆ haloalkylthio R¹¹ and R¹² together with the carbon atom to whichthey are attached may also be a carbonyl group, a 1,3-dioxoiane,1,3-dithiolane, 1,3-oxothiolane, 1,3-oxothiane, 1,3-dithiolane or a1,3-dithiane ring, where the 2-position of the six rings mentioned isidentical to the carbon atom to which R¹¹ and R¹² are attached, R⁹ andR¹³ or R¹⁰ and R¹⁴ may be a C₁-C₄-alkylene chain, or R¹⁰ and R¹² or R¹²and R¹³ together may form a π bond.